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Fun in Key West Podcast

🌴 Welcome to the Fun in Key West Podcast! 🌴Get ready to dive into all things Key West—the southernmost island where the sunsets are breathtaking, the food is unforgettable, and the drinks are always cold! 🍹In this podcast, we bring you insider tips on:✅ The best places to eat (yes, there will be conch fritters 🥥).✅ Where to drink and enjoy the island's famous cocktails 🍸.✅ The coolest spots to stay, from cozy inns to luxury getaways 🏝️.✅ And so much more—from quirky local events to can't-miss festivals! 🎉We'll also keep you up to date on the latest happenings around the island and occasionally chat with special guests who know Key West like the back of their sandy hand. 🐚Whether you're planning your first trip, a frequent visitor, or just daydreaming about island life, this podcast is your ultimate guide to enjoying paradise.🎙️ New episodes every wek—so don't forget to subscribe! Hit the like button if you're as obsessed with Key West as we are, and share the island love

Publisher-supplied feed metadata · PodParley refreshed Jun 12, 2026 · Source feed

  1. 100

    Key West in July: Key Lime Festival, 4th of July, Hemingway Days & Lobster Mini Season

    Key West in July: Key Lime Festival, 4th of July, Hemingway Days & Lobster Mini Season Host Michele O'Connor introduces the Fun in Key West podcast and shares an insider guide to visiting Key West in July, emphasizing the heat, humidity, and typical afternoon showers during hurricane season, along with tips on packing breathable clothes, reef-safe sunscreen, and planning around the weather with air-conditioned breaks. She highlights July's slower tourist pace, warm water, and major events including the five-day Key Lime Festival (through July 5) with tastings, a sip-and-stroll, and contests; 4th of July celebrations including a Truman Little White House cookout (July 3) and the Rotary Club 5K at Higgs Beach (July 4); Hemingway Days (July 21–26) featuring the Sloppy Joe's lookalike contest, running of the bulls, and a 5K; and lobster mini season (July 29–30). She recommends local museums and indoor spots, advises skipping rental cars, spotlights sponsor Danger Charters, and promotes her weekly newsletter and swag-box trivia. 00:00 Welcome to Key West 01:26 July Episode Preview 04:43 Sponsor Danger Charters 05:29 July Vibe and Tips 07:05 Weather and Packing 09:10 Beat the Heat Indoors 10:34 Why Visit in July 12:36 Key Lime Festival Guide 13:54 Fourth of July Events 14:53 Hemingway Days Highlights 17:02 Lobster Mini Season 18:14 Getting Around in Summer 19:17 More July Events List 21:07 Wrap Up and Newsletter 23:42 Final July Recap   www.funinkeywest/danger www.funinkeywest.com      

  2. 99

    Nick Shuck on The Green Flash at Sunset: Reinvention, Key West Grit, and Hope

    Nick Shuck on The Green Flash at Sunset: Reinvention, Key West Grit, and Hope Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and introduces the June 2026 book club pick, The Green Flash at Sunset by Nick Shuck, with Shuck joining to discuss the story behind the story, why Key West is a "world capital of reinvention," and how a book can feel dark yet hopeful. Shuck shares his background as a Pensacola senior English teacher, tour company owner (Emerald Coast Tours), father, and writer inspired by Hemingway, and explains he began the novel from its ending, sparked by watching Mallory Square street performers. He describes the green flash as a metaphor for chasing dreams despite risk and uncertainty, talks about crafting four central characters and Key West as an essential setting with layered history, and addresses reader reactions to the book's darkness as honesty about the world. The episode also spotlights sponsor Cruises and Tikis of Key West and mentions Key West Island Books. 00:00 Welcome to Fun in Key West 01:26 June Book Club Preview 03:13 Meet Author Nick Shuck 04:30 Nick's Origin Story 08:06 Cruising Tikis Sponsor Break 09:32 How Green Flash Began 12:53 Meaning of the Green Flash 16:37 Key West as Reinvention 21:07 Seeing Places in Layers 24:29 Meet Janet and Her Fight 27:11 Dark Stories Hopeful Endings 31:23 Writing Without an Outline 33:14 Endings and Lessons Learned 35:36 Writing Is Showing Up 37:17 Starting Emerald Coast Tours 38:50 Segway Tours Spark 40:44 Pub Tours Drunk History 42:07 Characters Walk Into Bar 43:22 Reinvention And Past 46:16 What Readers Should Feel 48:42 Next Projects And Research 51:06 Key West Favorites Rapid Fire 54:49 Coffee Rum And Local Tips 59:44 Thanks Sponsors And Wrap 01:02:40 Final Outro And Call To Action https://emeraldcoasttours.net/ https://bookshop.org/shop/PanhandleBooks    

  3. 98

    Historic Marker Monday: Truman's Little White House (Marker #59) in Key West

    Historic Marker Monday: Truman's Little White House (Marker #59) in Key West Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and spotlights Historic Marker Monday episode #59: the Harry S. Truman Little White House in Truman Annex. She describes the house's origins (built in 1890 as Quarters A and B, becoming a single-family residence by 1911) and notable early stays, including President William Howard Taft's 1912 visit and Thomas Edison's six-month World War I stay. The episode focuses on Truman's 11 working vacations from 1946–1953 totaling 175 days, when major issues were discussed there, including the Marshall Plan, Truman Doctrine, recognition of Israel, civil rights executive orders, the Korean War ceasefire efforts, and the merger creating the Department of Defense. She notes later presidential connections (Eisenhower, Kennedy, Carter, Clinton) and promotes Trusted Tours' small-group "White Glove Tour," featuring behind-the-scenes access, exhibits, refreshments, a keepsake, and a ride in Truman's 1950 Lincoln limousine. 00:00 Welcome to Fun in Key West 01:26 Marker Monday Setup 04:30 Sponsor White Glove Tour 05:45 Origins of the House 06:54 Early VIP Visitors 08:18 Truman Arrives in 1946 09:53 Big Decisions Made Here 12:11 Truman Daily Rhythm 14:00 Other Presidential Ties 15:31 Why Historic Markers Matter 17:00 Tour Highlights and Questions 19:15 Explore More Key West Markers 20:24 Final Wrap and Call to Visit   www.funinkeywest.com/truman

  4. 97

    Wreck Ashore: How Key West Wreckers Built a Fortune

    Wreck Ashore: How Key West Wreckers Built a Fortune Host Michele O'Connor introduces the Fun in Key West podcast and explains Key West's historic wrecking industry, highlighted by Historic Marker #58 near Mallory Square and the Wrecker Memorial by the Memorial Sculpture Garden. She describes wrecking as licensed marine salvage under maritime law—rescuing crews first, salvaging cargo, and settling claims through admiralty court at the Custom House—rather than piracy, noting myths like false lights lack evidence. The Florida Keys' reefs, storms, and limited navigation led to frequent wrecks, with NOAA estimates of hundreds to over 1,000 shipwrecks and an average of one per week in the 1800s; wrecking drove 60–90% of Florida exports by the 1830s and made Key West a leading port and home to Florida's first millionaire. She recommends visiting the Key West Shipwreck Museum tower, the Mel Fisher Museum about the 1622 Atocha found in 1985, and other related sites, and notes lighthouses and navigation improvements ended wrecking's profitability. 00:00 Welcome to Key West 01:26 Wreck Ashore Hook 03:18 Historic Marker 58 06:29 What Wrecking Means 08:04 Why Ships Wrecked Here 10:38 Key West Gets Rich 12:34 Custom House and Courts 15:01 Myths and Methods 18:45 Mel Fisher and Atocha 20:57 Shipwreck Museum Tower 21:42 End of Wrecking Era 22:43 Where to See It Today 24:33 Final Thoughts and Wrap 28:18 Recap and Call to Action  

  5. 96

    Key West in June: Weather, Packing Tips, Events, and a 3-Day Itinerary

    Key West in June: Weather, Packing Tips, Events, and a 3-Day Itinerary Host Michele O'Connor introduces the Fun in Key West podcast and shares a practical guide to visiting Key West in June, covering warm, humid upper-80s weather, comfortable water temps, and typical quick afternoon showers during the start of hurricane season. She recommends booking midweek for better hotel deals, packing breathable clothes, comfy shoes, reef-safe sunscreen, a hat, a refillable water bottle, and light rain gear, and planning outdoor activities earlier in the day. June highlights include Pride Month events, water excursions (snorkeling, kayaking, sandbar trips, dolphin watching, sunset cruises), Old Town staples like Mallory Square and Duval Street, beaches (noting possible sargassum), museums and historic sites, and day trips like Dry Tortugas (book early). She lists June 2026 happenings (Walk on White, Comedy Key West shows, farmers market, jazz jams, Mango Mania) and offers rainy-day indoor options plus a sample 3-day itinerary. Sponsor: Up the Keys Tours. 00:00 Welcome to Key West 01:26 June Trip Overview 03:48 Why Visit in June 05:50 Weather and Rain 07:33 What to Pack 08:51 Pride and Events 09:39 Best Things to Do 12:59 Museums and Day Trips 15:09 June 2026 Calendar 18:10 Rainy Day Plans 19:30 Where to Stay 21:21 Getting There 21:45 Three Day Itinerary 24:26 Final June Tips 25:31 Wrap Up and Thanks   https://funinkeywest.com/key-west-in-june/ www.funinkeywest.com/up  

  6. 95

    The Ultimate Couples Guide to Key West: Sunsets, Food Tours, and Quirky Date Ideas

    The Ultimate Couples Guide to Key West: Sunsets, Food Tours, and Quirky Date Ideas Host Michele O'Connor introduces the Fun in Key West podcast as an insider guide to where to eat, drink, stay, and what to do on the island, then focuses on experiencing Key West as a couple with a laid-back, spontaneous vibe. She recommends balancing iconic activities—Mallory Square Sunset Celebration, sunset cruises (Fury's Commotion on the Ocean, Flora Days, and Danger's Wind and Wine Sail), and Duval Street strolling—with unique options like ghost tours, cocktail classes, jet ski tours, kayaking, and private sandbar charters with Make It So Charters. Additional highlights include the Butterfly and Nature Conservatory (including flamingo meet-and-greets), Fort Zachary Taylor, Dry Tortugas, West Martello Tower, Hemingway Home, Truman Little White House, Audubon House, Rodriguez Cigars, Key West Island Bookstore, and date ideas like brunch, dessert stops, and wine at Vino's. The episode is sponsored by Key West Food Tours, promoting multiple tours and emphasizing booking ahead, staying hydrated, wearing comfortable shoes, avoiding driving, and planning one main activity per day. 00:00 Welcome to Key West 01:26 Couples Episode Setup 02:09 Key West Food Tours 05:03 Island Vibe for Two 07:05 How We Plan Days 09:20 Classic Sunset Staples 11:41 Duval and Food Tours 14:32 Cocktails and Water Fun 17:09 Nature and History Stops 19:06 Quirky Finds and Books 20:59 Dates and Itineraries 24:45 Practical Trip Tips 27:37 Sponsor and Farewell   www.funinkeywest.com/foodtour www.funinkeywest.com https://www.keywestcookingshow.com/     Other episodes to check out -   Key West Trip Recap: Coconut Beach Resort, Hidden Gem Cocktail & Cooking Classes, and Local Favorites Exploring Key West: From Sunrise to Sunset with Fun in Key West      

  7. 94

    Family-Friendly Florida Keys Road Trip: Key Largo to Key West (Summer Travel Tips)

    Family-Friendly Florida Keys Road Trip: Key Largo to Key West (Summer Travel Tips) Host Michele O'Connor introduces the Fun in Key West podcast and shares family-travel tips for a Florida Keys road trip from Key Largo to Key West heading into Memorial Day weekend 2026. She argues the Keys are a great multi-generational destination if approached with a relaxed mindset: plan one major activity per day, build in pool/beach downtime, pack snacks and water, plan around morning weather and afternoon showers, and check age/height requirements and booking needs. Suggested stops include Key Largo's John Pennekamp Coral Reef State Park (snorkeling or glass-bottom boats); Islamorada's Rain Barrel Village (Betsy lobster), Robbie's tarpon feeding, and Theater of the Sea; Marathon/Middle Keys attractions like the Turtle Hospital, Dolphin Research Center, aquarium, Pigeon Key/Seven Mile Bridge history, and Sombrero Beach; Duck Key's Hawks Cay Resort; Bahia Honda State Park; Big Pine Key's Key Deer Refuge; and Key West activities such as the conch train/trolley, Fort Zachary Taylor, Eco-Discovery Center, splash park, Southernmost Point replica, Butterfly Conservatory, aquarium, Hemingway Home, Shipwreck Museum, Mallory Square sunset celebration, and Dry Tortugas. The episode is sponsored by Fury Water Adventures. 00:00 Welcome to Key West 01:26 Family Trip Overview 02:28 Travel Tips and Sponsor 06:22 Keys Trip Mindset 07:43 Key Largo Adventures 09:48 Islamorada Road Stops 14:17 Marathon and Middle Keys 19:35 Lower Keys Highlights 21:49 Key West With Kids 28:06 Key West Eats and Treats 29:42 Dry Tortugas Day Trip 30:25 Sample Road Trip Itinerary 31:18 Final Tips and Wrap Up 35:45 Closing Thanks and Goodbye   www.funinkeywest.com/fury

  8. 93

    David Sloan Returns: How Key West Killed JFK, Bum Farto, Beatles Tales, and Haunted History

    David Sloan Returns: How Key West Killed JFK, Bum Farto, Beatles Tales, and Haunted History Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and interviews returning guest David Sloan, a longtime Key West author and researcher known for haunted history, Robert the Doll, and key lime pie expertise. Sloan explains how he moved to Key West after seeing ghost tours abroad and describes his work as entertainment-driven historical storytelling, including a personal connection to the Civil War fort where Robert the Doll is housed. They discuss his book How Key West Killed JFK, prompted by FBI files from research into missing fire chief Bum Farto and by JFK-assassination documents tying figures like Jack Ruby and Lee Harvey Oswald to the Keys; Sloan also details suspect Gilberto Lopez, newly found photos, and information from Lopez's daughter. He previews upcoming books on Bomfarto and The Beatles' 1964 Key West stay, addresses evolving ghost lore and misconceptions about Robert the Doll, shares local recommendations, and notes where to find him, his books, and tours, with sponsorship from iWitness Crime Tours. 00:00 Welcome to Key West 01:27 Meet David Sloan 02:20 Sponsor Crime Tour 05:57 David Origin Story 07:07 Mystorian Mindset 08:23 Guided to Key West 09:10 Why Write JFK Book 09:31 Bum Farto Files 10:47 Key West JFK Links 13:57 Cold War Power Players 17:25 Writing Without Conspiracies 18:40 Gilberto Lopez Breakthrough 24:42 Mafia Culture Revealed 27:22 Digging Unredacted Files 29:07 Hoffa and Teamsters Tales 31:54 Audience Q and Pivot 32:23 Prolific Books and Hits 33:48 Bucket List Lifestyle Brand 35:00 Tutu Hemingway Cat Story 36:36 Key Lime Passion Project 37:19 Key Lime Pie Debate 38:25 Best First Book Picks 40:17 Bonfardo Mystery Unpacked 45:58 Beatles Hurricane Detour 50:14 Haunted Research Origins 54:03 Robert the Doll Truths 58:04 Stories Still to Chase 58:55 Key West Food Favorites 01:01:51 Where to Find David 01:05:27 Final Thanks and Sponsor   www.funinkeywest.com/crime-tour   Grab a copy of the book over at Amazon (Click Here) As an Amazon Affiliate I will earn a commission on qualified purchases, at no extra charge to you.  It helps support our little corner of the world.  

  9. 92

    Visiting Key West in May: Weather, Events, Packing Tips, and Travel Planning

    Visiting Key West in May: Weather, Events, Packing Tips, and Travel Planning Host Michele O'Connor introduces the Fun in Key West podcast and shares an insider guide to visiting Key West in May, calling it a sweet spot with fewer crowds, mid-80s daytime highs, upper-70s evenings, less rain, and generally more forgiving hotel rates before hurricane season begins June 1. She covers what to pack (reef-safe sunscreen, hat, breathable clothes, comfortable shoes, lightweight jacket, reusable water bottle) and how to get there by driving the Overseas Highway, flying into the updated Key West International Airport, or taking the Key West Express ferry. Lodging choices depend on desired vibe and proximity to Duval. Recommended activities include Mallory Square Sunset Celebration, Fort Zachary Taylor Historic State Park, booking Dry Tortugas far in advance, museums, and water excursions. May highlights include Songwriters Festival, Walk on White, First Fridays on Fleming, markets, Monday night jazz jams, and the Schooner Wharf Minimal Regatta. Tips include skipping a rental car, not overpacking, not overplanning, and hydrating. 00:00 Welcome to Key West 01:26 Why Visit in May 04:49 May Weather Guide 06:35 What to Pack 08:48 Getting to Key West 11:44 Where to Stay 14:38 Must Do Highlights 18:23 May Events Calendar 23:46 Perfect May Day Plan 24:48 Common Travel Mistakes 27:32 Wrap Up and Resources 29:20 Final Farewell https://funinkeywest.com/key-west-in-may/    

  10. 91

    Historic Marker Monday: Key West's Old Stone Church (Marker #55)

    Historic Marker Monday: Key West's Old Stone Church (Marker #55) Host Michele O'Connor introduces the Fun in Key West podcast and a Historic Marker Monday episode focused on historic marker #55, the Old Stone Church (United Methodist Church) at 600 Eaton Street at Simonton and Elizabeth in Old Town. She explains how Methodist missionaries began services in 1832 in Bahamian settler Samuel Kemp's home for 12 years before a series of wooden church buildings were damaged by fire and hurricanes. Commissioned around 1870, architect William Kerr built the current coral-rock church by quarrying stone on the grounds and constructing it around the existing wooden church, later dismantling the interior structure after the roof went on in 1884. The quarry became a rainwater cistern, and 1950s excavation revealed the church sits on a small cemetery. The church remains active, with some Kemp descendants still attending, and listeners are directed to FunInKeyWest.com for a free walking tour and newsletter trivia drawing. 00:00 Welcome to Fun in Key West 01:26 Historic Marker Monday Begins 03:34 Finding the Old Stone Church 04:26 Key West in the 1800s 05:21 From Living Room to Churches 07:10 Building in Coral Rock 09:01 Cistern and Cemetery Surprise 10:07 Visit Today and Location Tips 11:06 Walking Tour and Newsletter 12:26 Final Wrap Up and Goodbye  

  11. 90

    Key West's Hidden WWII Submarine Base, Sonar School, and the Truman Annex

    Fun Fact Friday: Key West's Hidden WWII Submarine Base, Sonar School, and the Truman Annex Host Michele O'Connor introduces a "Fun Fact Friday" episode focused on Historic Marker #57 near the Outer Mole and the US Coast Guard Cutter Ingham Museum area, explaining how today's calm Truman Annex was once a major WWII submarine hub. She describes the site's evolution from the 1845 Fort Zachary Taylor Army installation to Navy control, the construction of five metal finger docks for submarines, and Key West's wartime role countering German U-boats that sank thousands of ships, including nearly 50 off Florida in 1942. Key West submarines escorted supply convoys and helped support the Pacific War, while the Fleet Sonar School relocated there in 1940, training thousands in sonar. The base was designated in 1946, became obsolete with nuclear submarines, and was decommissioned in 1974, later transforming into today's parks, amphitheater, cruise-ship pier, and tourist area. 00:00 Welcome to Fun in Key West 01:26 Episode teaser WWII waters 02:50 Fun Fact Friday kickoff 03:51 Marker 57 location today 05:17 Base origins and docks 07:12 U-boats off Florida 08:42 Key West wartime missions 10:08 Sonar school revolution 11:22 Decommission to Truman Annex 13:09 Questions and reflections 14:29 Live comments and travel tips 17:25 Final recap and subscribe  

  12. 89

    Mile Marker Zero: William McKeen on Key West's Wild 1970s Creative Scene

    Mile Marker Zero: William McKeen on Key West's Wild 1970s Creative Scene Host Michele O'Connor introduces the Fun in Key West podcast and welcomes William McKeen, Boston University journalism professor and author of Mile Marker Zero, to discuss 1970s Key West and the artists, writers, musicians, and actors drawn to its cheap, funky, under-the-radar culture. McKeen explains his drive as a lifelong storyteller, how Tom Corcoran (author of The Mango Opera) inspired and enabled the book after sharing a final Hunter S. Thompson message about documenting the "missing" Key West years, and why Corcoran became the narrative gateway linking figures like Thomas McGuane, Jim Harrison, Russell Chatham, Jimmy Buffett. They discuss balancing revelry with serious creative work, editing out some raunchier material (with extras on McKeen's website), Key West's sensory pull and rising costs, and the book's themes of friendship, survival, and tragedy, including Corcoran's missing wife. 00:00 Welcome to Fun in Key West 01:26 Episode teaser and guest 02:12 Podcast theme and intro 03:10 Meet author William McKean 04:40 Addicted to storytelling 07:24 Hunter Thompson voicemail 10:45 Writing Mile Marker Zero 11:59 Keeping the art focus 14:57 Why Key West drew artists 17:49 Then vs now costs 22:29 Structuring the big cast 26:17 Cut scenes and bonus tales 28:23 Wild stories reaction 28:49 Wild Key West Tales 29:36 Why Editors Matter 32:04 Sex Drugs and Context 33:24 Keeping Key West Lit 35:34 Writing With Senses 38:25 Friendship and Survival 41:34 Paradise With a Price 45:39 Can Creativity Return 48:11 Coffee Dinner and Favorites 50:52 Key West State of Mind 53:27 Final Thanks and Signoff https://www.williammckeen.com/ https://funinkeywest.com/fun-in-key-west-book-club/    

  13. 88

    Mouth-Numbing Relaxation Without the Hangover (with Kalm with Kava CEO Morgan Smith)

    Mouth-Numbing Relaxation Without the Hangover (with Kalm with Kava CEO Morgan Smith) Host Michele O'Connor introduces the Fun in Key West podcast as an insider guide to Key West food, drinks, events, and local guests, then interviews Morgan Smith, CEO of Kalm with Kava, about kava as a non-alcoholic alternative. Morgan shares how, after negative experiences with benzodiazepines and avoiding dependency, he found kava's relaxing, euphoric effects without hangovers or physical addiction and later took over his late friend Mike's kava company, expanding a Hawaii farm from 100 to about 15,000 plants. They explain kava's 3,000-year South Pacific cultural role, preparation as a root tea, expected mouth numbness and relaxation from key kavalactones, differences among noble vs "two-day" kavas, sourcing by region (Vanuatu, Fiji, Tonga/Hawaii), bar ordering basics, ethical sourcing, market demand, and beginner advice to start with a sampler pack. 00:00 Welcome to Key West 01:26 Meet Morgan and Kava 05:19 Morgan's Origin Story 11:11 What Kava Actually Is 15:22 How It Feels 17:10 First Time Tips 19:37 Kava vs Alcohol 23:12 What Kava Is Not 26:40 Noble vs Two Day 29:24 Nighttime Kava Choices 30:40 Kava Cultures Compared 32:55 Farming Cycles and Shortages 34:14 Island Mindset on Money 36:53 Why Kava Demand Surged 38:58 Ethical Sourcing Matters 41:20 Beginner Kava Roadmap 43:38 Ordering at Kava Bars 45:33 Kava History and Migration 49:18 Botany and Plant Varieties 52:01 Personal Wind Down Ritual 52:59 Hawaiian Harvest Plans 54:38 Alternatives and Farewell 57:24 Final Wrap and Subscribe https://kalmwithkava.com/  

  14. 87

    Historic Marker Monday: The Forgotten Key West Salt Ponds

    Historic Marker Monday: The Forgotten Key West Salt Ponds Host Michele O'Connor introduces the Fun in Key West podcast and, for Historic Marker Monday, explores Key West's largely forgotten 1800s salt-pond industry, when salt was essential for preserving food and enabling trade before refrigeration. Wealthy businessman and shipwreck-auctioneer Richard Fitzpatrick bought about 100 acres of southeast-end wetlands in 1830, built coral-walled drying pans with floodgates, and produced salt through tidal seawater and sun-driven evaporation, yielding typically 15,000–25,000 bushels annually and once 75,000. The venture was highly weather-dependent; Fitzpatrick left after about four years, though others continued until the Civil War disrupted production, which later resumed. A devastating 1876 hurricane washed away 15,000 bushels and effectively ended the industry. The historic marker stands at 2100 Flagler Avenue by Key West High School. 00:00 Welcome to Fun in Key West 01:26 Key West's Forgotten Gold 03:28 Historic Marker Monday Setup 04:45 Why Salt Mattered 06:27 Fitzpatrick Builds Salt Ponds 07:42 How Salt Was Made 09:42 Profit and Weather Risks 13:17 Civil War and Comeback 14:20 Hurricane Ends the Industry 15:08 Marker Location Today 16:07 Why This History Matters 17:29 Where to Learn More 18:47 Final Toast and Subscribe  

  15. 86

    Why Are There So Many Roosters in Key West? The Wild, Historic Story

    Why Are There So Many Roosters in Key West? The Wild, Historic Story Host Michele O'Connor introduces the Fun in Key West podcast as an insider guide to where to eat, drink, stay, and what to do in Key West, with updates on festivals and guests such as locals and business owners. This episode answers a frequent visitor question: why roosters and chickens roam Key West. She explains they're descended from birds kept by early settlers for eggs and meat, later added by Cuban immigrants, and tied in part to cockfighting; when cockfighting was outlawed and backyard chickens were less needed, many birds were released, creating today's feral population. The warm climate, few predators, and easy access to food help them thrive, though feeding is discouraged and can bring fines. She describes a local love-hate relationship and notes the city and the Key West Wildlife Center have humanely managed the issue by rescuing, trapping, and relocating over 15,000 birds to mainland free-range properties. 00:00 Welcome to Key West 01:28 Rooster Question Setup 01:56 Podcast Theme Song 02:45 Why So Many Roosters 04:39 Roosters Everywhere 06:22 Origins and History 08:12 Why They Thrive 09:18 Love Hate Reality 10:44 City Management Efforts 12:58 Wildlife Center Relocation 14:28 Why Locals Still Love Them 15:48 Myths vs Facts 17:33 Wrap Up and Subscribe 18:26 Final Outro www.funinkeywest.com  

  16. 85

    Cheapest Places to Live in the Florida Keys (and What "Cheap" Really Means)

    Cheapest Places to Live in the Florida Keys (and What "Cheap" Really Means) Host Michele O'Connor answers questions about what it really takes to live in the Florida Keys, emphasizing that "cheap" is relative and the Keys are expensive compared to national averages. She outlines factors beyond listing price—rent, property taxes, insurance (including flood), maintenance from salt air, storm prep, commute, home condition, and lifestyle goals—then compares areas often discussed for budget-conscious moves: Big Pine Key for a quieter, nature-focused lower-Keys lifestyle with fewer conveniences; Tavernier as an overlooked upper-Keys option with easier mainland access; Marathon as a centrally located middle-Keys choice with wide price variation by neighborhood and property type; Key Largo as convenient but usually pricier; Key West as iconic but typically among the most expensive; and Stock Island as a potentially more realistic alternative near Key West. She encourages realistic expectations, research, and choosing best value and fit. 00:00 Welcome to Fun in Key West 01:26 Episode Topic Living in the Keys 03:53 Setting Realistic Cost Expectations 08:10 What Affordable Really Means 10:39 Big Pine Key Nature and Value 12:32 Tavernier Upper Keys Option 14:26 Key Largo Convenience Costs More 16:02 Marathon Middle Keys Balance 18:10 Key West and Stock Island Alternatives 22:31 Hidden Costs and Smart Planning 24:23 Quick Shortlist and Takeaways 26:58 Wrap Up Resources and Goodbye 28:33 Final Encouragement and Call to Action www.funinkeywest.com  

  17. 84

    Key West in April: Conch Republic Days, Markets, Music & Travel Tips

    Key West in April: Conch Republic Days, Markets, Music & Travel Tips Host Michele O'Connor introduces the Wandering Wednesday episode focused on visiting Key West in April, highlighting ideal weather, outdoor activities, and a packed events calendar. She points listeners to funinkeywest.com for the event calendar and notes schedules can change. Major April highlights include Conch Republic Independence Days with opening ceremonies, a street fair, the Cow Key 0K, a Mallory Square sea battle with stale Cuban bread, parades, and parties; plus art walks (Walk on White), farmers markets, Comedy Key West shows, jazz events, Glow Hour at the Studios rooftop, and Howard Livingston at the Tennessee Williams Theater. She advises booking Dry Tortugas (Yankee Freedom) well in advance, planning around the April 11 Seven Mile Bridge Run road closure, and booking lodging early for big events like Conch Republic Days and the late April/early May Songwriters Festival, with packing and transportation tips for crowds and parking. 00:00 Welcome to Fun in Key West 01:26 April Trip Preview 02:41 Wandering Wednesday Kickoff 04:09 Why April Works 07:15 Dry Tortugas Planning 08:22 April Weather Snapshot 09:16 Conch Republic Days 11:50 More April Events 14:17 Travel Styles and Tips 16:30 Packing and Getting Around 18:06 Wrap Up and Community www.funinkeywest.com  

  18. 83

    Key West Trip Recap: Coconut Beach Resort, Hidden Gem Cocktail & Cooking Classes, and Local Favorites

    Key West Trip Recap: Coconut Beach Resort, Hidden Gem Cocktail & Cooking Classes, and Local Favorites Host Michele O'Connor and her husband Kevin from Out A Here Travel recap a quick Key West trip, sharing planning tips like booking direct flights into the new Key West airport and using Lyft over taxis. They review staying at the quiet, no-frills Coconut Beach Resort (a timeshare where third-party bookings may require switching rooms) and highlight meals and drinks at Flaming Buoy Filet Company, Conch Republic, Miso Happy, Sloppy Joe's, Green Parrot, Bali Bar, and the Tipsy Rooster. Key stops include Mallory Square sunset viewing tips amid seawall repairs, Key West Candle & Bath Company, Island Bookstore's Fun in Key West book club display, the San Carlos Institute, the Shipwreck Museum tower, and Doing Work Coffee. They praise the Key West Cooking Show's cocktail class and lunch cooking show featuring Cuban dishes and Italian-meringue key lime pie, plus note seasonal orchids, a temporary Southernmost Buoy replica, and rising airfare costs. 00:00 Welcome to Fun in Key West 01:26 Trip Recap Kickoff 03:18 Flights and New Airport 05:07 Coconut Beach Resort Stay 09:38 Flaming Buoy Supper Club 12:13 Mallory Square Sunset Tips 15:01 Local Shops and Book Club 17:47 Conch Republic Fish Sandwich 18:58 Cocktail Class Hidden Gem 25:20 Miso Happy Outdoor Seating 26:09 San Carlos Cuban History 27:22 Cooking Show and Key Lime Pie 32:56 Rotating Menu Tips 33:18 Shipwreck Museum Tower 34:06 Wrecking History Gold 35:36 Cooking Show Swag 37:01 Wrecker Towers Explained 38:23 Favorite Bars Debate 42:03 Doing Work Coffee Stop 45:06 Duval Street Changes 46:05 Trip Recap Resources 47:37 Orchid Season Photos 52:20 Airport Rides Savings 54:03 Travel Prices Advice 56:52 Final Thanks Farewell   www.outaheretravel.com www.funinkeywest.com  

  19. 82

    Preserving Key West's Soul: Nick Green on the Old Island Restoration Foundation, the Oldest House, and Iconic Home Tours

    Preserving Key West's Soul: Nick Green on the Old Island Restoration Foundation, the Oldest House, and Iconic Home Tours Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and interviews Nick Green, executive director of the Old Island Restoration Foundation (OIRF), a nonprofit founded in 1960 to preserve Key West's historic wooden district, architecture, culture, and history. Nick shares his background in international development and philanthropy, how he and his wife fell in love with Key West, and what drew him to preservation work, including an effort to pursue UNESCO Creative City recognition. He explains OIRF's role operating the Oldest House Museum & Gardens since 1974, its community programs for children, and events such as the Key West Home Tour and conch shell blowing contest rooted in the island's wrecking industry history. The episode also covers planned upgrades, accessibility, staffing and volunteers, funding through admissions, memberships, donations, and venue rentals, and Nick's favorite local spots. 00:00 Welcome to Fun in Key West 01:28 Meet Nick Green 04:21 Nick's Global Background 06:51 Falling for Key West History 09:15 UNESCO and Museum Realities 11:21 What OIRF Does 11:34 Origins in 1960 13:45 Oldest House Becomes Mission 16:10 Programs and Signature Events 17:22 Oldest House Visitor Tips 19:46 Captain's Family and House Move 20:55 Cookhouse and Climate Design 22:24 Upgrades and Restoration Plans 25:01 Accessibility and Small Team 26:46 Funding and Home Tours 27:32 How the Tours Work 29:24 Schedule Pricing and Upgrades 31:12 Choosing Homes and Volunteers 33:05 Conch Shell Contest Origins 36:28 Why Preservation Matters 38:27 Ways to Support OIRF 41:28 Local Favorites QandA 44:00 Events Rentals and Admissions 46:52 Final Thanks and Wrap Up 49:41 Host Closing Message https://oirf.org/ www.funinkeywest.com  

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    Pit Bulls in Paradise: Tony Soika on Key West Mysteries, Rescue Dogs, and Second Acts

    Pit Bulls in Paradise: Tony Soika on Key West Mysteries, Rescue Dogs, and Second Acts Host Michele O'Connor introduces the Fun in Key West Podcast and its Book Club episode featuring author Tony Soika, a retired U.S. Army officer with 30 years of service and extensive animal-rescue volunteering. Soika discusses his deep pull toward the Florida Keys since first visiting in 1999, his transition challenges after leaving the military, and how becoming a late-in-life father shaped him and influenced his writing. He explains how his novel Pit Bulls in Paradise (first in the Conch House Chronicles) follows retired officer John Tuttle in the Keys as he uncovers a dogfighting ring after pit bulls with fighting injuries arrive at a shelter, reflecting Soca's real-life rescue of a pit bull and his advocacy that "there are no bad dogs, only bad owners."  00:00 Welcome to Fun in Key West 01:26 Meet Tony Soika 04:09 Tony's Life and Dogs 05:03 Why the Keys Call You 07:31 Fatherhood and Inspiration 10:04 From Coaching to Novels 12:14 Why Pit Bulls in Paradise 13:43 Rescuing Honey Bear 16:26 Building John Tuttle 19:28 Veteran to Civilian Shift 21:38 Finding Identity in Key West 23:21 Dogs Feel Our Pain 25:00 Why Animal Cruelty Matters 27:33 Setting the Story in Key West 29:08 Making Key West Feel Real 30:30 John the Reluctant Hero 31:50 Next Book Afghanistan Thread 33:55 Key West Signings and Support 35:58 Rescue Dogs and Local Favorites 40:25 Book Heart and Real Cameos 44:06 Where to Follow and Final Wrap  

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    Historic Marker Monday: How Cayo Hueso Became Key West

    Historic Marker Monday: How Cayo Hueso Became Key West Host Michele O'Connor introduces the Fun in Key West podcast and this Historic Marker Monday episode focused on the origin of Key West's name, highlighted by a historic marker near Mallory Square. She explains how the Taíno word "cayo" (small island) passed through Spanish usage and into English as "key," and how "hueso" (bone) made the original Spanish name Cayo Hueso translate to "Bone Island." Michele shares theories for the island's bones, including Native American conflicts, shipwreck victims from the "graveyard of the Atlantic," and fishbone piles, noting settlers found large bone piles in the 1820s. She describes how American mapmakers misheard and simplified the name into "Key West," mentions Spanish speakers still use Cayo Hueso, and promotes self-guided walking tours, a Key West book club reading Pit Bulls in Paradise with an upcoming author interview, and a forthcoming map of historic marker locations. 00:00 Welcome to Fun in Key West 01:27 Historic Marker Monday Begins 01:46 Why Key West Has Its Name 03:39 Mallory Square Marker Hunt 06:10 Cayo to Key Language Shift 07:36 Bone Island Theories 10:05 How Cayo Hueso Became Key West 10:51 Cultural Blend and Fun Facts 13:34 Tours Book Club and Marker Map 16:45 Final Wrap and Next Time  

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    Historic Marker Monday: Ponce de León's 1513 Voyage

    Historic Marker Monday: Ponce de León's 1513 Voyage and Key West's Marker #50   Host Michele O'Connor  introducses this Historic Marker Monday episode focused on a Duval Street historic marker (noted at 1405 Duval Street) honoring Spanish explorer Ponce de León and his 1513 voyage. She recounts his background sailing with Columbus, his roles in the Dominican Republic and Puerto Rico, and how he personally financed three ships to seek gold, expand Spain's territory, and strengthen his position. The episode traces the expedition as he named Florida, moved through the Florida Keys (Los Martires), reached the mainland, encountered conflict with Indigenous people and took captives, then traveled to the Dry Tortugas for food but no fresh water, and was pushed by the Gulf Stream to Cuba—an accidental discovery valuable to navigation. Michelle explains why this history connects to Key West and encourages listeners to visit marker #50 and use funinkeywest.com for tours, a marker map, and a virtual book club. 00:00 Welcome to Fun in Key West 01:26 Historic Marker Monday Setup 03:07 March Check In and Marker Location 05:41 Who Was Ponce de Leon 06:54 Mission and Fleet Goals 08:21 Naming Florida La Florida 09:37 Fresh Water Stops and Survival 10:18 Reaching and Naming the Keys 12:27 West Coast Landfall and Conflict 13:42 Dry Tortugas and Provisioning 15:22 Gulf Stream Discovery and Return 16:52 Final Colonization Attempt 1521 18:39 Why It Matters to Key West 19:50 Wrap Up and Key Takeaways 22:00 Explore More Tours and Book Club 23:23 Final Outro and Next Time www.funinkeywest.com  

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    Tasty Tuesday: The Best Oyster Spots in Key West

    Tasty Tuesday: The Best Oyster Spots in Key West (Happy Hours, Hidden Gems & Upscale Bites) Host Michele O'Connor delivers a Tasty Tuesday guide to why oysters in Key West "hit different," emphasizing freshness from local fishermen, the Historic Seaport, and markets like Eaton Street Seafood Market. She shares what to look for in a great oyster stop—freshness, variety, preparation styles, atmosphere, value (especially happy hour), and seafood focus—then highlights recommended spots including Half Shell Raw Bar, Alonzo's Oyster Bar, Conch Republic Seafood Company, Schooner Wharf, Thirsty Mermaid, Two Friends Patio, Island Dogs, Pepe's Cafe, and upscale options like A&B Lobster House, Little Pearl, Cafe Marquesa, and Prime Steakhouse, plus Stock Island stops like Matt's Stock Island and Hogfish Bar & Grill. She offers oyster-ordering tips, suggests building an "oyster crawl," notes honorable mentions, and directs listeners to funinkeywest.com for guides, tours, and a book club. 00:00 Welcome to Fun in Key West 01:26 Tasty Tuesday Oyster Tease 03:50 Why Key West Oysters Shine 05:20 How to Pick a Spot 06:47 Seaport Oyster Classics 10:29 Old Town Hidden Gems 12:27 Upscale Oyster Nights 14:06 Stock Island and Markets 15:25 Ordering and Pairing Tips 17:11 Build Your Oyster Crawl 18:26 Honorable Mentions and Wrap 20:08 More Guides and Farewell 21:36 Final Recap Outro www.funinkeywest.com  

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    Bottling the Spirit of Key West with Deejay Peak of Key West Candle & Bath Co.

    Bottling the Spirit of Key West with Deejay Peak of Key West Candle & Bath Co. Host Michele O'Connor introduces the Fun in Key West podcast as an insider guide to where to eat, drink, stay, and what to do in Key West, with updates on events and local guests. She interviews Deejay Peak, owner of Key West Candle and Bath Company, who moved to Key West seven and a half years ago after family trips and an opportunity to run her parents' ice cream shop. Deejay describes starting her candle business with $500 by collecting top-shelf liquor bottles from local bar dumpsters, then rebranding into frosted jars and later redesigning packaging with hand-drawn Key West-inspired art. She discusses using premium soy wax and clean fragrances influenced by her daughter's asthma, expanding into soaps and other bath products, and opening a working studio retail shop at 1011 Whitehead Street. DJ shares bestsellers like the Blue Heaven scent, travel-friendly packaging options, where she likes to eat and drink, how to order online or wholesale, and a discovery kit for sampling scents. 00:00 Welcome to Key West 01:26 Meet Deejay Peak 03:39 WiFi Woes and Shop Local 05:06 From Ice Cream to Candles 06:27 Dumpster Bottle Origins 07:16 Rebrand for Key West Vibes 08:55 Island Life vs Mainland 10:41 The Broken Candle Story 12:19 Clean Soy Candle Quality 12:47 Getting Into Local Shops 15:41 Expanding Into Bath Products 17:11 Opening a Storefront 18:17 Getting the Studio Space 18:38 Inside the Working Shop 19:08 Must Buy Travel Picks 20:33 Blue Heaven Best Seller 22:01 Hours and Family Help 22:55 Family First Business 24:25 Creating Real Connection 26:09 Key West Food Favorites 28:25 Coffee and Porch Ritual 29:04 How to Order Online 31:02 Book the Trip Wrap Up 32:47 Final Thanks and Recap www.funinkeywest.com https://keywestcandleandbathco.com/  

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    Thirsty Thursday: Best Frozen Drinks in Key West

    Thirsty Thursday: Best Frozen Drinks in Key West (Flying Monkeys, Fat Tuesday & Mary Ellen's) Host Michele O'Connor introduces the Fun in Key West podcast as an insider guide to where to eat, drink, stay, and what to do on the island, with updates on events and occasional local guests. In this Thirsty Thursday episode, she spotlights Key West's frozen drink scene and encourages listeners to try new menu options beyond standard pina coladas, margaritas, and daiquiris. She recommends Flying Monkeys on Duval (near Bull and Whistle and Fogerty Mansion) for its mix-and-match frozen machines, to-go cups, and drinks like the Flying Monkey (spiked lemonade plus raspberry-bourbon) and a frozen White Russian, plus a non-alcoholic Monkey Slush. She also covers Fat Tuesday's New Orleans-style daiquiri wall, and Mary Ellen's off Duval for its dive-bar vibe and her favorite frozen Irish coffee topped with crushed cookies. She mentions other Key West cocktail history, Better Than Sex dessert-and-drinks, and directs listeners to funinkeywest.com for guides and the book club. 00:00 Welcome to Fun in Key West 01:26 Thirsty Thursday kickoff 03:02 Frozen drinks mindset 04:02 Flying Monkeys favorites 07:15 Fat Tuesday daiquiri wall 08:29 Mary Ellens Irish coffee 10:05 More bars and history 11:25 Better Than Sex detour 12:39 Guides and book club 13:54 Wrap up and sign off www.funinkeywest.com  

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    Trust the Signs: Mark Renson on How Will I Know, Whitney Houston as a Guardian Angel, and Finding Solace in the Florida Keys

    Trust the Signs: Mark Renson on How Will I Know, Whitney Houston as a Guardian Angel, and Finding Solace in the Florida Keys   Host Michele O'Connor introduces chef, restaurant owner, and author Mark Renson about his novel How Will I Know, the Fun in Key West Book Club February pick. Renson shares his background as owner of Ambition Coffee and Eatery in upstate New York (nearly 26 years), his first book Is The Coffee Fresh? about daily life in his coffee house and how he was inspired in 2012 to write fiction using Whitney Houston as a guardian angel.   He explains how he began the novel in 2016, wrote in small increments until COVID gave him time to finish, and realized he was pulling heavily from his own life experiences, including a breaking point during the recession when his restaurant carried $80,000 in debt. Renson recounts a pivotal moment at the Florida Bay in Key Largo where, after praying for help, he felt a wind and heard a message he interpreted as God being present; within 15 days his debts were resolved or put on manageable payment plans, and he later secured a publishing contract.   He also describes finding a key in downtown Memphis in 2011 and, two weeks later, being asked by Bradley Cooper to feed him a paleo diet for seven weeks while filming The Place Beyond the Pines—an experience that changed his reputation and financial stability. Renson discusses his belief that there are no coincidences, his training in holistic classes and identification as a psychic medium (though he does not offer readings), and his practice of asking the universe for specific signs; he cites examples such as Whitney Houston songs appearing at meaningful moments and a COVID-era idea to create Baileys-infused 'boozy muffins' that went viral and helped sustain his business.   The conversation covers Renson's love of the Keys—especially Key Largo for its quiet, reflection, and 'church' feeling—along with favorite local spots like Key's Bite (steak a Mexicana), his mixed feelings about busy Key West, and places he revisits like Blue Heaven (his husband's favorite), LaTe Da, Mallory Square sunsets, and occasional stops on Duval Street.   Renson confirms several characters and details are based on his life (including Lucy, inspired by his longtime friend Tracy), explains the Dolly Parton inspiration behind the name 'Ambition,' and shares how he researched Whitney Houston's voice, mannerisms, and outfits over many years. He addresses the inclusion of other entertainers in a seance scene, his belief that Whitney 'picked' them, and notes his decision to keep the story feel-good. Renson lists where to buy the book (Amazon, Barnes & Noble by order, markrenson.com, and select Florida Keys locations including Shell World, the Marathon library, and Books & Brews at Florida Keys Brewing Co.), mentions upcoming Restaurant Week dates and plans to run a Disney 5K in April, and names Whitney Houston songs like 'I Wanna Dance with Somebody' as spirit-resetting favorites. The episode closes by reinforcing the theme of trusting signs, self-trust, resilience, and the Florida Keys as a grounding backdrop.   00:00 Welcome to Fun in Key West: What This Podcast Is All About 01:26 Today's Guest Tease: Mark Ranson, the Keys & a Whitney Houston Guardian Angel 02:10 Theme Song + Book Club Intro: Why "How Will I Know" Hits Different 04:16 Meet Mark: Chef, Restaurant Owner & Accidental Author 07:15 Writing Fiction During COVID: How Michael Monroe Became Mark's Story 09:33 The 2010 Breaking Point in the Keys: Florida Bay, Faith & the Wind 12:25 The Key That Opened Doors: Memphis Find to Feeding Bradley Cooper 14:05 Self-Doubt, Failure & Trusting the Message Behind the "Feel-Good" Book 16:46 Why Whitney Houston? Mediumship, Signs, Dreams & Listening to the Higher Voice 22:39 Ambition Coffee & Eatery: Dolly Parton Inspiration and the Restaurant's Soul 26:04 So Why Key Largo? Solace, Stillness, and Feeling Close to God 26:27 The Florida Keys as Church: Finding Solace & Spiritual Reset 27:13 Quieting the Mind: Raising Your Vibration & Noticing the Signs 27:58 Dockside Wildlife Moments (and the Dolphin TikTok Story) 29:03 Real-Life Lucy: Tracy, 50 Years of Friendship & Accents 30:04 Foodie Favorites in Key Largo: Key's Bite, Steak a Mexicana & Local Vibes 30:51 Key West Takes: Crowds, Duval Street, and Sunset at Mallory Square 34:34 No Coincidences: How to Ask for Signs (Songs, Keys, Dreams) 38:13 Sparkles, Endings & Sequel Talk: Where Whitney Could Return 39:19 Nailing Whitney on the Page: Outfit Research, Voice, and Concert Deep Dives 41:20 What's Next for Mark: Restaurant Week, Disney 5K, and the Séance Entertainers 45:07 Where to Buy the Book + The One Song That Resets Your Spirit (Final Wrap) 48:38 Closing Message: Trust the Universe & Keep Chasing the Signs www.funinkeywest.com https://marcrenson.com/  

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    Key West Travel Tips and Booking Smarter with Savvy.com (Guest: Eric Goldreyer)

    Key West Travel Tips and Booking Smarter with Savvy.com (Guest: Eric Goldreyer) Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and interviews hospitality entrepreneur Eric Goldreyer, who has 30+ years of experience spanning bed and breakfasts, boutique hotels, mega-yacht inflatables, and vacation rental property management. Eric shares his background (founding BedandBreakfast.com, selling it to HomeAway in 2010; co-founding TurnKey Vacation Rentals and selling to Vacasa in 2021; and launching FunAir) and explains why he created Savvy.com after experiencing high platform fees when booking a trip. He outlines common frustrations with Airbnb/VRBO and other OTAs, including 15–20% platform fees, restricted guest-host communication, temporary phone numbers, and complications when changes are needed (similar to booking hotels via Expedia). Eric describes Savvy as a book-direct marketplace that avoids platform fees, shows Savvy pricing alongside Airbnb pricing, and focuses on enabling direct communication with professional property managers (no rent-by-owner listings), with internal vetting and planned third-party trust/ID verification for hosts and travelers. The conversation covers how travelers can avoid scams by checking reviews, what fees are normal (taxes and cleaning) versus frustrating (platform fees), and why professional local management helps during high-demand destinations like Key West. Eric notes Savvy has been live about a year, lists about 150,000 North American properties from 2,500+ property management companies, is adding thousands of listings monthly, and aims to expand internationally by year-end, sharing how to reach him via Savvy.com, LinkedIn, and [email protected]. 00:00 Welcome to Fun in Key West: What This Podcast Covers 01:26 Today's Guest: Hospitality Veteran Eric Goldreyer Joins the Show 02:00 Theme Song & Kickoff: Setting the Island Vibe 03:26 Eric's Origin Story: BedandBreakfast.com to Boutique Hotels 04:36 From Mega-Yacht Inflatables to Vacation Rental Tech 05:40 Why Savvy.com Exists: Beating Airbnb/VRBO Fees 07:42 Behind the Scenes of OTAs: Hidden Fees & Blocked Communication 10:49 Avoiding Scams: Reviews, Vetting, and Booking with Pros 14:42 What Fees Are Legit vs. Junk Fees (and Price Comparison Tools) 17:40 How Travel Has Changed: From Hospitality to Transaction 18:19 Tech vs. Hospitality: Why Human Hosts Still Matter 19:09 Real-World Trip Planning: Nuance, Off-Market Homes & Concierge Help 21:02 Savvy for Peak Season: Direct Communication + No Rent-by-Owner Safety Net 23:01 Quality Control: Reviews, Background Checks & Removing Bad Apples 24:47 Key West Love Letter: B&Bs, Longer Stays & Local Vibes 28:15 Food, Coffee & Duval Street: Gluten-Free Finds and Must-Do Spots 30:23 Booking Habits to Break: Save Money by Booking Direct on Savvy 31:55 Wrap-Up: Savvy's Growth Plans, How to Reach Eric, and Final Thanks www.funinkeywest.com www.savvy.com  

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    First Timer Friday: Why Marathon Is the Perfect Home Base in the Florida Keys

    First Timer Friday: Why Marathon Is the Perfect Home Base in the Florida Keys   Host Michele O'Connor welcomes listeners to the Fun in Key West podcast and presents a First Timer Friday episode that detours from Key West to highlight Marathon as a laid-back, centrally located Florida Keys home base. She explains Marathon's position halfway between Miami and Key West across 13 islands and why it offers quieter mornings, easier parking, and strong water access for day trips up to Key Largo, Island Morada, Big Pine Key, and Key West. Activities and highlights include snorkeling at Sombrero Reef, kayaking and paddleboarding on both ocean and bay sides through mangroves and seagrass with possible manatee, turtle, and bird sightings, and fishing options (deep sea, reef, and flats). She recommends experiencing the Seven Mile Bridge via the old bridge for walking, biking, fishing, and views, plus visiting Pigeon Key by trolley for tours, museum history, snorkeling, and fishing while bringing your own essentials. Wildlife stops include the Dolphin Research Center's educational and conservation focus and the Turtle Hospital's guided tours and rehabilitation work, with advice to book ahead and consider supporting both. She also spotlights Curry Hammock State Park for trails, kayaking, picnics, birdwatching, and competitive seasonal camping. For food, she recommends Keys Fisheries for marina views and classic Keys atmosphere, noting popular items like the lobster Reuben, seasonal stone crab claws, and award-winning key lime pie, along with a cash-only note and arriving early for sunset. The episode closes by describing who Marathon best fits (families, nature lovers, water-focused travelers) versus those seeking nightlife or luxury, and directs listeners to funinkeywest.com for guides, an ultimate road trip guide, newsletter (including a Key West happy hour list), and book club updates. 00:00 Welcome to Fun in Key West: What This Podcast Covers 01:26 Today's Detour: Why Marathon Is a Hidden Gem in the Keys 02:57 First Timer Friday: Marathon as the Perfect Home Base 04:12 Where Marathon Sits + Why the Middle of the Keys Matters 06:29 Snorkeling in Marathon: Easy Reefs, Clear Water & Tour Tips 08:03 Kayaking & Paddleboarding: Mangroves, Manatees and Quiet Water 09:30 Fishing Capital Vibes + Experiencing the Seven Mile Bridge 10:42 Pigeon Key: Old Bridge Walks, History Tours & Island Time 11:38 Wildlife Must-Dos: Dolphin Research Center & The Turtle Hospital 13:13 Curry Hammock State Park: Trails, Camping and Nature Escapes 14:11 Where to Eat in Marathon: Keys Fisheries & Local Favorites 15:17 Is Marathon Right for You? Day Trips, Travel Styles & Final Take 17:30 Wrap-Up + Resources: Guides, Newsletter, Happy Hour List & Book Club 19:08 Final Outro: Marathon, the Unsung Hero of the Florida Keys www.funinkeywest.com  

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    Historic Marker Monday: The Birth of the Conch Republic and the Great Battle of 1982

    Historic Marker Monday: The Birth of the Conch Republic and the Great Battle of 1982   Host Michele O'Connor introduces the Fun in Key West podcast and a Historic Marker Monday episode about the 1982 events that led to the creation of the Conch Republic. She recounts how a U.S. Border Patrol roadblock at Last Chance Saloon in Florida City stopped and searched every car entering and leaving the Keys, creating massive traffic jams, generating national and international press, and causing major economic harm as tourists canceled trips and hotels sat empty. After community leaders pushed Mayor Dennis Wardlow to respond, a legal effort led by David Paul Horan failed in federal court in Miami; outside the courthouse Wardlow told reporters Key West would "go home and secede." On April 23, 1982, the Conch Republic declared itself, raised its flag over City Hall, and staged a humorous protest known as the "Great Battle of the Conch Republic," involving the schooner Western Union (captained by John Cross) jokingly attacking the U.S. Coast Guard cutter Diligence with water balloons, conch fritters, and stale Cuban bread, while the cutter responded with fire hoses. Wardlow, now acting as prime minister, immediately surrendered and requested foreign aid and war relief; the episode notes they are still waiting to be paid, but the roadblock was removed and tourism was saved. The script emphasizes the protest was not anti-American and the Coast Guard was never considered an enemy, describing the Conch Republic as a "sovereign state of mind" rooted in humor, community, and independence. Listeners are directed to the historic marker at 402 Wall Street and invited to attend Conch Republic Days, described as the 44th year of the celebration, with 2026 dates April 17–26, 30+ events, multiple parades (including one spanning from the Atlantic to the Gulf), and a reenactment at Mallory Square featuring boats, water balloons, stale bread, a Coast Guard fire hose response, and a plane dropping toilet paper. The episode points viewers to funinkeywest.com for details, free guides, a newsletter, and the podcast's book club and author interviews on YouTube, including a 2025 selection by Richie "Conch Boy" Gomez. 00:00 Welcome to Fun in Key West: What This Podcast Covers 01:26 Historic Marker Monday Teaser: The Conch Republic Origin Story 02:57 March 1982: The Border Patrol Roadblock & 17-Mile Traffic Jam 05:45 Tourism Takes a Hit: Empty Hotels and Economic Fallout 07:05 From Courtroom to Secession: 'We're Going Home and Secede' 07:56 April 23, 1982: Flag Raised & The 'Great Battle' (Water Balloons + Cuban Bread) 09:33 Quiet Victory: Roadblock Removed and the Real Point of the Protest 10:51 Conch Republic Today: A 'Sovereign State of Mind' + Where to See the Marker 11:36 Conch Republic Days 2026: Dates, Parades, and the Battle Reenactment 13:25 Wrap-Up & Where to Learn More (Website, Guides, YouTube, Newsletter) 14:16 Final Sendoff: Keep the Conch Republic Spirit Alive www.funinkeywest.com  

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    Exploring Key West in February: Festivals, Events, and Warm Weather Delights

    Exploring Key West in February: Festivals, Events, and Warm Weather Delights In this episode of the Fun in Key West podcast, host Michele O'Connor offers a comprehensive guide to enjoying Key West in February. From highlighting warm weather and sunny skies to detailing a variety of festivals and events including arts and crafts fairs, theaters, Mardi Gras celebrations, and foodie exhibitions, Michele provides valuable insider tips for both first-time visitors and Key West veterans. The episode also discusses upcoming key events and attractions throughout the month, including the Red Barn Theater's plays, various tribute band performances at the Key West Theater, and the Smithsonian-sponsored food history exhibit. Tune in to discover why February is an ideal time to visit Key West and how to make the most out of your island getaway. 00:00 Welcome to Fun in Key West Podcast 01:26 First Timer Friday: Why Visit Key West in February? 04:50 February Events and Activities in Key West 06:16 Key West Arts and Entertainment Highlights 10:57 Wrapping Up: Stay Connected and Informed www.funinkeywest.com  

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    Crispy Conch Fritters and Key West Delights: Tasty Tuesday Special

    Crispy Conch Fritters and Key West Delights: Tasty Tuesday Special In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a culinary journey through Key West, with a focus on the iconic conch fritters. Michele covers everything from the perfect texture and seasoning of these crispy treats to the best spots on the island to enjoy them. She also dives into the origins of conch fritters, their preparation, and tips for ensuring you get the best ones. Whether you're planning a visit to Key West or simply daydreaming about island life, this episode is packed with insights and recommendations to savor the tastes of paradise. 00:00 Welcome to Fun in Key West Podcast 01:26 Tasty Tuesday: Conch Fritters Introduction 04:39 The Perfect Conch Fritter: What to Look For 09:17 Top Spots for Conch Fritters in Key West 12:56 Tips for Enjoying Conch Fritters 16:06 Wrapping Up: Join Us Next Time www.funinkeywest.com  

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    Exploring Clinton Square: A Civil War Landmark in Key West

    Exploring Clinton Square: A Civil War Landmark in Key West In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to Key West, focusing on Clinton Square's rich and layered history. She highlights its significance during the Civil War as the only southern city occupied by the Union throughout the conflict. Michele explains the unique dual commemoration within Clinton Square, where both Union and Confederate memories are honored in the same space, making it a fascinating site of coexistence and historic significance. The episode encourages listeners to slow down and appreciate the history surrounding them, with tips on exploring more historic markers in Key West. 00:00 Welcome to Fun in Key West Podcast 01:28 Historic Marker Monday Introduction 01:49 Exploring Clinton Square's Civil War History 06:36 Union and Confederate Memorials in Key West 09:38 Key West's Military Significance 11:09 Wrapping Up and Exploring More Markers www.funinkeywest.com  

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    Discovering Key West with Salty Paw Charters

    Discovering Key West with Salty Paw Charters In this episode of the Fun in Key West podcast, host Michele O'Connor dives into the idyllic world of Key West with Zach from Salty Paw Charters. Learn about Zach's journey from aspiring teacher to captain, and how he launched his own charter business in Key West. The episode explores unique experiences offered by Salty Paw Charters, including sandbar adventures, brunch cruises, sunset charters, and a new family-friendly pirate-themed scavenger hunt. Discover what sets Salty Paw Charters apart, the breathtaking sights, and the must-bring essentials for your trip. Get insider tips on local dining and enjoy a special offer to save on your next Key West adventure. 00:00 Welcome to Fun in Key West Podcast 01:26 Introducing Zach from Salty Paw Charters 03:37 Zach's Journey to Becoming a Captain 06:04 Unique Offerings of Salty Paw Charters 10:56 Experiencing Key West Sandbars 15:13 Sunset and Brunch Cruises 19:17 Upcoming Pirate Adventure for Families 22:06 Tips for a Great Charter Experience 24:59 Zach's Personal Favorites in Key West 27:02 Conclusion and Special Offers   SALTYDEAL to save $100 www.funinkeywest.com https://saltypawskeywest.com/    

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    Discovering the Hidden Gems of Key West: West Martello Tower

    Discovering the Hidden Gems of Key West: West Martello Tower In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a journey to explore the transformation of the West Martello Tower, a Civil War fort that has been reclaimed by nature and community efforts. From its initial construction in 1862 to its current status as a lush garden and butterfly habitat managed by the Key West Garden Club, Michele delves into the rich history and vibrant present of this unique landmark. Whether you're a history buff, nature lover, or just looking for a serene escape, this episode offers a fascinating look at one of Key West's hidden gems. Tune in to learn more about its indestructible design, historical significance, and the dedicated community that keeps its legacy alive. Plus, get insider tips for your next Key West adventure. 00:00 Welcome to Fun in Key West Podcast 01:26 Exploring the West Martello Tower 02:59 Historic Marker Monday: West Martello's Rich History 08:26 West Martello's Modern Transformation 10:10 Visiting the West Martello Today 14:26 Conclusion and Key West Adventures www.funinkeywest.com  

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    First Timer's Guide to Choosing Bed and Breakfasts in Key West

    First Timer's Guide to Choosing Bed and Breakfasts in Key West In this episode of the 'Fun in Key West' podcast, host Michele O'Connor offers practical tips and historical insights for selecting the perfect bed and breakfast in Key West. She covers essential considerations such as location, amenities, and the unique characteristics of various Key West properties. Michele delves into the history of Key West's hospitality and provides a rundown of specific accommodations, touching on their individual quirks and advantages. She also addresses factors like breakfast offerings, room comfort, and additional fees. Listeners are encouraged to reach out for personalized recommendations and visit the Fun in Key West website for more travel tips and ideas. 00:00 Welcome to Fun in Key West Podcast 01:26 Choosing the Perfect Bed and Breakfast 02:32 First Timer Friday Tips 03:59 Key Considerations for Your Stay 05:48 Understanding Breakfast Options 07:36 Location, Location, Location 10:01 Amenities and Must-Haves 12:40 Room Comfort and Style 16:03 Adult-Only vs. Social Vibes 17:09 Fees, Rates, and Hidden Costs 18:38 Historical Stays in Key West 20:03 Narrowing Down Your Options 25:13 Final Tips and Resources www.funinkeywest.com  

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    Exploring Key West's Best Breakfast Spots: A Tasty Tuesday Guide

    Exploring Key West's Best Breakfast Spots: A Tasty Tuesday Guide In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to the best breakfast spots in Key West. From iconic locations like Blue Heaven and Pepe's Cafe to hidden gems like Sandy's Cafe and Glazed Donuts, Michele lists must-try places that offer delicious breakfast options. Additionally, she introduces the different 'Key West Breakfast Personalities,' including the Slow Sipper, Recovery Specialist, Brunch Maximalist, and Local Looper. Michele offers pro tips on avoiding the breakfast rush and maximizing your morning meal experience in Key West. The episode also highlights where to find the best coffee and cocktails, and emphasizes that vacation calories don't count. Listeners are encouraged to visit funinkeywest.com for more guides, tips, and foodie inspiration. 00:00 Welcome to Fun in Key West Podcast 01:28 Exploring Key West Breakfast Spots 06:10 Iconic Key West Breakfast Experiences 07:33 Coffee First: Key West's Best Cafes 10:17 Vacation Calories Don't Count: Indulgent Breakfasts 12:28 Healthy Options and Vegetarian-Friendly Spots 13:33 Breakfast with a View: Scenic Spots 14:31 Finding Your Key West Breakfast Personality 16:16 Tips for Enjoying Breakfast in Key West 21:36 Conclusion and Community Engagement www.funinkeywest.com  

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    Embracing the Pirate Spirit: A Conversation with Author Chris Harvey

    Embracing the Pirate Spirit: A Conversation with Author Chris Harvey In this episode of the Fun in Key West podcast, host Michele O'Connor chats with author Chris Harvey about his book 'Son of a Son of a Pirate' and its sequel 'One Particular Harbor.' Chris shares his writing journey, inspiration from Jimmy Buffett, and his love for pirate history. The episode offers insights into the characters, plot development, and the significance of family legacy. Chris also discusses his favorite Key West spots and plans for a third book. Tune in for an engaging discussion about living life on your own terms and embracing the pirate spirit. 00:00 Welcome to Fun in Key West Podcast 01:26 Introducing Special Guest: Chris Harvey 03:34 Chris Harvey's Journey and Inspirations 05:11 Family Legacy and Maritime Adventures 08:03 The Influence of Jimmy Buffett 12:44 Crafting a Multi-Timeline Pirate Tale 17:35 The Human Side of Blackbeard 23:12 Righteous Thieves and Modern-Day Robin Hoods 23:40 Casting the Movie Adaptation 24:58 The Sequel: One Particular Harbor 27:40 Writing the Third Book 29:00 Key West Book Tour and Favorite Spots 36:46 The Cinematic Writing Style 39:22 Where to Find the Books 40:13 Final Thoughts and Farewell www.funinkeywest.com  

  38. 63

    Best Brunch Spots in Key West: A Tasty Tuesday Adventure

    Best Brunch Spots in Key West: A Tasty Tuesday Adventure Welcome to Fun in Key West podcast with Michele O'Connor, your friendly guide to exploring Key West. This episode, part of the 'Tasty Tuesday' series, is dedicated to uncovering the best brunch spots in Key West. Whether you prefer casual eateries, upscale dining, or boozy brunches, Key West has it all. Michele highlights local favorites such as Blue Heaven, Bagatelle, Pepe's, Hot Tin Roof, and many more, offering mouth-watering dishes from lobster benedict to key lime crepes. She also includes recommendations for healthy and vegetarian-friendly options and discusses places offering unique brunch experiences. Tune in for a delicious journey through Key West's vibrant brunch scene! 00:00 Welcome to Fun in Key West 01:26 The Magic of Brunch in Key West 03:21 Top Brunch Spots in Key West 13:14 Hidden Gems and Unique Brunch Experiences 20:08 Wrapping Up and Final Thoughts www.funinkeywest.com  

  39. 62

    Uncovering Key West History: The Yellow Fever Epidemic and Its Lasting Impacts

    Uncovering Key West History: The Yellow Fever Epidemic and Its Lasting Impacts In this episode of the Fun in Key West podcast, host Michele O'Connor explores a fascinating yet tragic chapter in Key West's history—the yellow fever epidemic during the Civil War. Discover the story behind the unmarked cemetery at 625 White Street, the resilience of the Key West community, and the significant impact on public health practices. Michele also delves into the historical connections to Fort Jefferson and Dr. Samuel Mud, who played a crucial role during the outbreak. Tune in for a deep dive into how this epidemic reshaped sanitation, medical research, and quarantine measures in the U.S. 00:00 Welcome to Fun in Key West Podcast 01:30 Exploring Key West's Yellow Fever History 03:00 Historic Marker Monday: Unmarked Cemetery 04:36 Impact of Yellow Fever on Key West 10:11 Fort Jefferson and Dr. Samuel Mudd 11:54 Key West's Historical Connections 16:43 Conclusion and Community Engagement www.funinkeywest.com  

  40. 61

    Empower Your Dreams: Making Your Destiny Happen with Donzel Leggett

    Empower Your Dreams: Making Your Destiny Happen with Donzel Leggett In this empowering episode of the Fun in Key West podcast, host Michele O'Connor brings on Donzel Leggett, a Key West native and author of 'Make Your Destiny Happen.' Donzel shares his inspirational journey from growing up in Key West to becoming a global leader. He talks about the importance of taking charge of one's life, developing a life plan, and the value of self-improvement. This episode is filled with practical advice on how to stop letting life happen to you and instead make life happen for you. Denzel also discusses his upcoming book signing at Books and Books in Key West on December 11, 2025. Tune in to be inspired to dream big and make this year your best yet.   00:00 Welcome to Fun in Key West 01:26 Introducing Our Special Guest: Donzel Leggett 03:54 Donzel's Journey from Key West to Global Leadership 10:31 The Inspiration Behind 'Make Your Destiny Happen' 17:31 Taking Control of Your Life: Practical Advice 22:14 Creating Competitive Advantage 22:36 The Destiny Development Delta Model 24:14 Escaping the 9 to 5 25:34 Defining Personal Success 28:22 Navigating Life's Peaks and Valleys 29:17 The Importance of Self-Assessment 33:16 Sustaining Your Goals 35:19 Book Tour and Hometown Pride 38:33 Final Thoughts and Gratitude www.funinkeywest.com Check out his Book here   Connect with Donzel Leggett:   / donzelleggett     / donzel.leggett.9     / destinydevdelta     / donzel_leggett      / @donzelleggett   https://feeds.captivate.fm/make-your-... https://www.destinydevdelta.com/ https://www.makeyourdestinyhappen.com 

  41. 60

    Exploring Key West: Lime, Crime, and Tour Adventures with Kim Stamps

    Exploring Key West: Lime, Crime, and Tour Adventures with Kim Stamps In this episode of the Fun in Key West podcast, host Michele O'Connor talks with Kim Stamps, a seasoned tour guide and business owner in Key West. They dive into Kim's unique journey from a finance graduate to operating popular tours in Key West, including the new Eyewitness True Crime Tour and Tart Tails Walking Tours. Kim shares about her experiences in the industry, the intricacies of starting and selling her first business, Up the Keys Tours, and the rich history and unique character of Key West. Listeners also get insights into what makes these tours special, along with some amusing anecdotes. The episode wraps up with some tips for visitors to Key West and a reminder that there's always time for limes and crime. 00:00 Welcome to Fun in Key West Podcast 01:26 Introducing Kim Stamps: A Journey of Adventure 05:18 The Challenges and Triumphs of Running a Tour Business 09:17 Eyewitness Crime Tour: Expect the Unexpected 18:38 Tart Tails Tour: A Sweet Slice of Key West History 20:54 Exploring Key Lime Pie Adventures 21:25 Combining Crime and Key Lime Pie Tours 23:04 Surprising Guests on Tours 24:41 Footwear for Walking Tours 25:54 Misconceptions About Key West Locals 27:43 Journey to Becoming a Tour Guide 29:21 Advice for Aspiring Tour Guides 32:00 Future Plans for Tours 33:48 Best Places to Eat in Key West 37:12 Final Thoughts and Custom Tours   www.funinkeywest.com   Book iWitness Crime Tour Here    

  42. 59

    Exploring the Historic Key West Aquarium: A Dive into Tourism History

    Exploring the Historic Key West Aquarium: A Dive into Tourism History   In this episode of Fun in Key West, host Michele O'Connor takes listeners on a historical journey through the Key West Aquarium. Michele uncovers how the aquarium, built in the 1930s with the support of the Works Progress Administration, became the first open-air aquarium in the United States and a pivotal point in the transformation of Key West into a tourism hotspot. The episode covers the challenges faced over the years, including hurricanes and economic shifts, and highlights the aquarium's role in educating and captivating visitors with its marine life exhibits. Michele also provides practical tips for exploring the aquarium today and invites listeners to connect through the Fun in Key West community.   00:00 Welcome to Fun in Key West Podcast 01:28 Exploring the Key West Aquarium 03:53 The Birth of Key West Tourism 07:14 Challenges and Resilience 10:04 Modern Day Aquarium Experience 13:23 Historic Marker Monday and Community Engagement 15:42 Conclusion and Next Steps   www.funinkeywest.com  

  43. 58

    Tasty Tuesday: The Ultimate Key West Waterfront Dining Guide

    Tasty Tuesday: The Ultimate Key West Waterfront Dining Guide In this episode of the Fun in Key West podcast, host Michele O'Connor takes listeners on a culinary journey through the best waterfront dining spots in Key West. From upscale experiences like Hot Tin Roof to casual beachside eats at Loggerheads Beach Bar, Michele shares insider tips on where to savor fresh seafood, exotic cocktails, and breathtaking ocean views. She also highlights the vibrant local food scene, with recommendations for various dining options, including brunch, lunch, and dinner spots. Tune in to discover the hidden gems and must-visit eateries to make your Key West trip deliciously unforgettable. 00:00 Welcome to Fun in Key West Podcast 01:26 Diving into Waterfront Dining 04:41 Hot Tin Roof: Sunset Vibes and Chic Island Experience 05:36 Sunset Pier: Iconic Views and Live Music 06:21 Seaside Cafe: Lobster Pizza and Southernmost Charm 07:26 Southernmost Beach Cafe: Fresh Fish and Margaritas 07:59 La Trattoria Oceanside: Italian Delights 08:21 Salute on the Beach: Lunch and Strolls 08:44 Loggerheads Beach Bar: Feet in the Sand 09:15 Geiger Key Marina: Old School Vibes 10:08 Boathouse Bar and Grill: Best Happy Hour 10:47 Hurricane Hole: Kayaks and Catch of the Day 11:18 Half Shell Raw Bar: Quintessential Key West 12:06 Conch Republic Seafood Company: Fresh Catch and Happy Hour 12:56 Fisherman's Cafe: Breakfast and Lunch with a View 13:50 Louis's Backyard: Brunch and Liquid Lunch 14:37 Latitudes: Ferry Ride to Sunset Key 15:19 Wrapping Up: More Key West Dining Tips 16:21 Join the Fun in Key West Community 17:17 Farewell and Final Thoughts   www.funinkeywest.com  

  44. 57

    Unveiling Key West: Your Ultimate Guide for January 2026

    Unveiling Key West: Your Ultimate Guide for January 2026 In this inaugural episode of the 'Fun in Key West' podcast for 2026, host Michele O'Connor serves as your vibrant guide to all things Key West. Michele covers a broad spectrum of topics such as where to eat, drink, stay, and enjoy in Key West, especially focused on January events. Listeners are introduced to the unique offerings and lesser-known gems of the island, including festivals like the Southernmost Regatta, Mile Zero Fest, and Key West Literary Seminar. Whether you're a local, a frequent visitor, or simply daydreaming of a tropical escape, this episode provides essential insights and updates to help you maximize your Key West experience. Highlights include a rundown of the weather, top activities, key places to visit, and upcoming events, blending practical advice with local flavor. 00:00 Welcome to Fun in Key West Podcast 01:35 Kicking Off Wandering Wednesday 2026 03:34 Why January is the Best Time to Visit Key West 09:10 Exciting Events in Key West This January 18:25 Wrapping Up and Final Thoughts   www.funinkewest.com  

  45. 56

    Discover Key West's Boathouse: Happy Hour and History Combined

    Discover Key West's Boathouse: Happy Hour and History Combined In this episode of the Fun in Key West podcast, host Michele O'Connor dives into one of Key West's most beloved happy hour spots, the Boathouse, which is located in the historic seaport. O'Connor shares insider details on their half-price small plates, waterfront views, and fascinating historical significance tied to the location. Listeners will learn about the Boathouse's move from Front Street to its current spot, popular menu items, and historical tidbits about the turtle corrals previously on-site. Michele also encourages listeners to join the fun at Fun in Key West, including signing up for the happy hour and book club lists, and participating in weekly trivia giveaways for a chance to win Key West swag. 00:00 Welcome to Fun in Key West Podcast 01:35 Thirsty Thursday: Happy Hour and History 03:13 Exploring the Boathouse 05:50 Boathouse Menu Highlights 07:38 Historic Seaport and Turtle Crawls 10:24 Join the Fun: Newsletters, Book Club, and More 12:01 Conclusion and Farewell   www.funinkeywest.com  

  46. 55

    December Delights in Key West: Your Ultimate Guide to Holiday Happenings

    December Delights in Key West: Your Ultimate Guide to Holiday Happenings In this episode of the Fun in Key West podcast, host Michele O'Connor provides an insider's guide to the vibrant December events in Key West and the Florida Keys. From holiday parades, boat parades, and festive light tours to concerts, art walks, and fishing tournaments, listeners will discover a plethora of activities to enjoy. Michele highlights key events such as the Key West Christmas Parade, the Key West Lighted Boat Parade, and various theater performances. She also shares tips on weather and packing for the trip, and encourages listeners to visit funinkeywest.com for more details and event updates. This episode is perfect for anyone planning a visit to Key West or simply daydreaming about a tropical holiday escape. 00:00 Welcome to Fun in Key West Podcast 01:35 Holiday Magic in Key West 02:57 December Events in Key West 04:55 Key West Holiday Activities 08:00 Upcoming Events and Activities 16:26 Wrapping Up and Final Thoughts                        

  47. 54

    Unveiling Key West's Civil War Legacy: The Story Behind the Blockade

    Unveiling Key West's Civil War Legacy: The Story Behind the Blockade In this episode of the Fun in Key West podcast, host Michele O'Connor explores Key West's surprising role during the Civil War. Dive into the history of the Union blockade, the strategic importance of Key West, and the role of British blockade running ships. O'Connor also provides insights into local historic markers and encourages listeners to explore these hidden stories through the self-guided walking tour. Additionally, listeners can sign up for the newsletter for trivia, happy hour tips, and a chance to win the monthly Key West surprise box. The episode wraps up with an invitation to join the free book club, featuring books connected to Key West. 00:00 Welcome to Fun in Key West Podcast 01:37 Historic Marker Monday: Key West in the Civil War 04:30 The Strategic Importance of Key West 07:56 The Role of Blockade Runners 09:11 British Involvement and Economic Impact 12:09 Exploring Key West's Historic Markers 14:24 Join Our Community and Stay Connected 15:52 Conclusion and Farewell   www.funinkeywest.com                      

  48. 53

    Exploring Key West: From Sunrise to Sunset with Fun in Key West

    Exploring Key West: From Sunrise to Sunset with Fun in Key West In this episode of Fun in Key West, host Michele O'Connor and her husband Kevin from Out A Here Travel, provide a comprehensive recap of their recent Key West adventure. They discuss updates at key locations like Pittsburgh International and Key West airports, and their stay at the Southernmost Beach Resort. The episode includes recommendations for dining, coffee spots, new breweries, and unique tours like the Eyewitness Crime Tour. They also touch on practical travel tips and changes to popular attractions and transit services. Whether you're a first-time visitor or a seasoned traveler, this episode offers valuable insights for your next Key West escapade.   00:00 Welcome to Fun in Key West Podcast 02:01 Special Guest: Kevin from Out of Here Travel 03:43 Travel Insights: Pittsburgh to Key West 04:58 Exploring the New Key West Airport 10:10 Staying at the Southernmost Beach Resort 13:50 Sunrise Photography and Resort Activities 19:15 Key West Coffee and Dining Options 20:40 Discovering the Southernmost Brewery 23:18 Eyewitness Crime Tour and Key Lime Pie Tasting 26:16 Exploring Local Dining Gems 27:47 Reviving Outta Here Travel 29:40 Cruising Adventures and Destinations 33:06 Key West Trolley and Transportation Tips 35:05 Changes at Kermit's Key Lime Pie Shop 36:32 Top 10 Things We Love About Key West 46:42 Final Thoughts and Travel Tips   https://funinkeywest.com/ https://www.outaheretravel.com/                      

  49. 52

    Exploring Key Largo: Your First Stop on the Road to Paradise

    Exploring Key Largo: Your First Stop on the Road to Paradise Join Michele O'Connor on the Fun in Key West podcast as she kicks off 'Wandering Wednesday' with a detailed exploration of Key Largo. Discover Key Largo's unique charm, from the underwater adventures at John Pennekamp Coral Reef State Park to bird-watching at the Laura Quinn Wild Bird Sanctuary. Learn about local tips for dining, happy hours, and nightlife, and get recommendations on where to stay. Whether it's your first visit or you're a seasoned traveler, Michele provides an insider's guide to maximizing your Key Largo experience. Complete with activity suggestions, nature spots, and sunset views, this episode is your ultimate guide to making the most of Key Largo before continuing your journey through the Florida Keys. 00:00 Welcome to Fun in Key West Podcast 01:35 Exploring Key Largo: First Stop on the Road to Paradise 02:06 Key Largo Daytime Adventures 14:54 Nightlife and Dining in Key Largo 20:28 Where to Stay in Key Largo 22:30 Best Time to Visit and Travel Tips 27:01 Conclusion and Community Engagement https://funinkeywest.com/ https://funinkeywest.com/fun-in-key-west-book-club/ https://funinkeywest.com/things-to-do-in-key-largo-at-night/  

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    Diving into Key West's Sponging History

    Diving into Key West's Sponging History Welcome to the Fun in Key West podcast, hosted by Michele O'Connor. In this episode with a fresh theme song and intro, Michele explores the fascinating history of the sponging industry in Key West. Discover how this unexpected industry blossomed in the 1820s, peaked in the 1890s, and eventually declined due to overharvesting and environmental damage. Learn about the economic impact on Key West, the influence of Greek divers, and the modern-day connections to this historic trade. Michele also highlights the importance of Key West's historic markers and encourages visiting funinkeywest.com for more information, including a self-guided walking tour, happy hour list, and book club. Tune in for a blend of history, local insights, and a celebration of Key West's unique culture. 00:00 Welcome to Fun in Key West Podcast 01:35 Historic Marker Monday: The Sponging Industry 04:12 The Rise and Fall of Sponging in Key West 11:46 Modern Connections to Key West's Sponging Past 14:14 Exploring Key West's Historic Markers 14:59 Stay Connected with Fun in Key West 15:58 Conclusion and Farewell   https://funinkeywest.com/ https://funinkeywest.com/fun-in-key-west-book-club/ https://funinkeywest.com/sponging-more-than-a-shopping-trip/  

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ABOUT THIS SHOW

🌴 Welcome to the Fun in Key West Podcast! 🌴Get ready to dive into all things Key West—the southernmost island where the sunsets are breathtaking, the food is unforgettable, and the drinks are always cold! 🍹In this podcast, we bring you insider tips on:✅ The best places to eat (yes, there will be conch fritters 🥥).✅ Where to drink and enjoy the island's famous cocktails 🍸.✅ The coolest spots to stay, from cozy inns to luxury getaways 🏝️.✅ And so much more—from quirky local events to can't-miss festivals! 🎉We'll also keep you up to date on the latest happenings around the island and occasionally chat with special guests who know Key West like the back of their sandy hand. 🐚Whether you're planning your first trip, a frequent visitor, or just daydreaming about island life, this podcast is your ultimate guide to enjoying paradise.🎙️ New episodes every wek—so don't forget to subscribe! Hit the like button if you're as obsessed with Key West as we are, and share the island love

HOSTED BY

Michele O'Connor

Frequently Asked Questions

How many episodes does Fun in Key West Podcast have?

Fun in Key West Podcast currently has 50 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Fun in Key West Podcast about?

🌴 Welcome to the Fun in Key West Podcast! 🌴Get ready to dive into all things Key West—the southernmost island where the sunsets are breathtaking, the food is unforgettable, and the drinks are always cold! 🍹In this podcast, we bring you insider tips on:✅ The best places to eat (yes, there will be...

How often does Fun in Key West Podcast release new episodes?

Fun in Key West Podcast has 50 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Fun in Key West Podcast?

You can listen to Fun in Key West Podcast on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Fun in Key West Podcast?

Fun in Key West Podcast is created and hosted by Michele O'Connor.
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