The Great Loop Podcast

Chris and Deb are back on the bridge with another Great Loop update—this time cruising from Amelia Island up into Brunswick, navigating rolly sounds, Coast Guard encounters, and even a close call in “Hell’s Gate,” before settling into the charm of Savannah and the iconic beauty of Hilton Head Island. From hidden gem restaurants and “Velcro marinas” to dolphin sightings, anchoring adventures, and a bucket-list golf tournament experience, this leg of the journey is packed with stories, laughs, and a few lessons learned along the way.

14 views Mar 23, 2026 Captain's LogChris and Deb are back on the move, wrapping up their Florida chapter with a jam-packed stretch of family visits, boating challenges, and a few unforgettable stops along the way. From a magical trip to LEGOLAND with the grandkids (complete with pirate treasure hunts and 32 million LEGO bricks!) to cruising past manatees, dodging tight channels, and even spotting gators by drone — this leg of the Great Loop had a little bit of everything.They share the realities of life on the water too — from pricey marina fuel and lost fishing rods to upgrading their onboard washer/dryer and navigating tricky tides along the Intracoastal. Plus, hear about their time at TPC Sawgrass, favorite waterfront restaurants, and what’s next as they head toward Savannah and Hilton Head. If you love boating, travel, or just good stories from the water — this one’s for you.

In this episode, Chris and Deb check in from a very cold and snowy Cincinnati after hopping off the boat for a quick Midwest pit stop (because apparently eight degrees sounded like a good idea).They recap the last couple of weeks aboard in Sanford, Florida, where life has been anything but boring. From learning to fly a brand-new drone over water (and surviving the backwards controls) to discovering hidden gems like the Old Jailhouse restaurant and local breweries, they’ve been soaking up everything this charming river town has to offer.Highlights from this episode include:Their first overnight anchorage at Butcher’s Bend — complete with alligators, manatees, glassy water, and incredible star-filled skiesExploring Winter Park and finding what might be one of the best steaks everTesting out alternative transportation options like bikes, rental cars, and the SunRailA competitive (of course) Topgolf outingMore fun at their favorite German spot, Hollerbach’sAnd a true boater lesson learned the hard way: always tie down the dinghy cover when 40+ mph winds are in the forecastThey also share what it’s like when a polar vortex makes its way to Central Florida — frozen hoses, icy dock lines, and a near $900 dinghy cover replacement that thankfully turned into a muddy but salvageable recovery mission.Looking ahead, family visits, a cruise up the St. Johns River, and dreams of anchoring off Harbour Town during tournament week are all on the horizon as they prepare to push north on the Great Loop.It’s everyday loop life — part adventure, part problem-solving, part golf, and always a good story.As always, thanks for tuning in and following along on the journey.

In this episode of the Great Loop podcast, we share a full update from Sanford, Florida, where we’ve taken a winter freshwater detour along the St. Johns River. We explore downtown Sanford, visit the Central Florida Zoo’s Asian Lantern Festival, tour Daytona International Speedway, scout fuel access by dinghy with close alligator encounters, and share favorite restaurants, golf courses, and marina tips. From boat projects to drone plans, this episode captures why Sanford is one of our favorite unexpected Great Loop stops.

In this episode, Chris and Deb check in from Florida with a story that perfectly captures the spirit of the Great Loop — part careful planning, part happy detour.They recap SeaDan’s time on the hard in Jacksonville, highlight standout boatyard work at Huckins, and share some favorite local discoveries, from golf courses and restaurants to an unexpected Jaguars game. Then the real adventure begins as they follow a weather window inland and head down the St. Johns River — a side trip that quickly becomes one of their favorite stretches of the entire Loop.Along the way, they anchor in remote jungle-like coves, spot manatees and their first alligator, cross Lake George on glassy water, and finally settle into Sanford, a historic river town that feels instantly like home. They talk marinas, river life, e-bike explorations, breweries, wildlife, and why letting the Loop wander often leads to the best memories.A relaxed, story-driven update filled with practical insights, favorite stops, and a reminder that sometimes the best moments come from listening to the weather and following curiosity.

 Hosts: Chris & Deb Winnenberg Release Date: October 14, 2025Description: Chris and Deb are back at the mic with stories that stretch from the banks of the Ohio River to the greens of TPC Sawgrass. In this episode, they revisit the riverside camp where their Great Loop dream first began 30 years ago — a sentimental stop that sparks memories of raising their kids on water-skis, campfires, and late-night laughter.From there, the journey winds south to stormy St. Augustine and its unexpected treasures — a classic car museum full of chrome nostalgia, a speakeasy hidden in a historic ice plant, and a five-star meal that made them laugh as much as it dazzled.The adventure continues north to Jacksonville Beach and Palm Cove Marina, where a chance encounter leads to golf clubs custom-built by a 50-year pro — and a surprise bar conversation with a former Lynyrd Skynyrd pianist who once opened for the Rolling Stones.Then it’s on to the bucket-list moment every golfer dreams of: playing the 17th-hole island green at TPC Sawgrass. Spoiler alert — neither Chris nor Deb make the green, but they walk away with a story that’s pure SeaDAN magic.Now back home in Cincinnati for the fall, they reflect on family, golf, and the joy of slowing down while C-DAN gets a little TLC at Huckins Boatyard. Looking ahead, they share plans to explore the St. Johns River — one of the few rivers in North America that flows south to north — before heading up the East Coast in 2026.

Chris and Deb are back with nearly 300 more miles under their keel! In this episode, they recap their journey from Fort Pierce to St. Augustine, with plenty of highlights along the way. Hear about surprise jewelry shopping and a great meal at 12A Buoy, a hot round of golf at the PGA Wanamaker Course, and an “oops” lesson in why you should always wash new boat fabrics. They also share their dinghy adventure to the Navy SEAL Museum and Little Jim’s, the thrill of watching a rocket launch in Titusville, and a full day exploring the Kennedy Space Center.The trip continues north with wildlife encounters and beach strolls in New Smyrna, a quick but delicious stop in Palm Coast, and finally, days of historic charm in St. Augustine—complete with trolley tours, Castillo de San Marcos, and prepping for a bucket-list tee time at TPC Sawgrass.It’s equal parts travelogue, boating lessons, and “did you see that?!” moments—classic Great Loop adventure storytelling.

Join Chris and Deb as they embark on an unforgettable journey through sunny Florida! From the vibrant streets of Fort Lauderdale to the serene beauty of the keys, and the charming allure of Fort Pierce, their adventure is packed with exciting experiences and breathtaking views. Don't miss out on their stories of exploration, fun, and discovery. Hit subscribe and join the adventure!

EPISODE SUMMARY:This week, we say goodbye to the Keys and make our long-anticipated jump up the coast to Fort Lauderdale! But not before a little sandbar party, brewery-hopping, a surprise manatee visit, and some world-class ribs courtesy of “Brisket Bob.”Join us as we:✔️ Hang at a 50-boat sandbar bash✔️ Discover Florida Keys Brewing Co. and Square Grouper✔️ Navigate a rental car fender bender✔️ Say goodbye to Todd & Tammy after an epic visit✔️ Refuel with 400 gallons of diesel 😳✔️ Dodge cruise ships on our way into Port Everglades Inlet✔️ Dock at Hall of Fame Marina — and watch Olympic divers from the boat✔️ Cruise Fort Lauderdale’s canals via dinghy✔️ Celebrate Deb’s birthday with golf at Fort Lauderdale Country Club✔️ End the day with homemade pasta, wine, and a front-deck sunset (with NO BUGS!)🧭 WHAT’S NEXT?We're planning dinghy runs through the New River to explore The Wharf, e-bike rides along the beach, and a slow climb north toward West Palm. Golf clubs in tow!📌 Don’t forget to SUBSCRIBE to follow our journey as we continue America's Great Loop aboard SeaDAN — one dock, dinghy, and dinner at a time.

This week on the Great Loop Podcast, Chris and Deb welcome special guests — Chris’s brother Todd and sister-in-law Tammy — for a full week of Keys fun, paddleboard spills, and waterfront memories aboard SeaDAN.

In this episode, Chris and Deb share their recent adventures in the Florida Keys, discussing their experiences exploring marinas, local attractions, and the unique lifestyle of living on a boat. They delve into the challenges and joys of traveling in the area, including their encounters with local culture, dining experiences, and outdoor activities like snorkeling and paddleboarding. The conversation highlights the beauty and excitement of life in the Keys, along with practical insights for fellow travelers.

After three sun-soaked weeks exploring the Florida Keys, Chris and the crew are back in Cincinnati—but not before making memories in Marathon and Islamorada. In this episode, we dive into the highs (and hilarious mishaps) of DIY scuba diving at Sombrero Reef, recount the best mini-golf course we've ever played, and share the story behind our accidental “Lost Buoy Dive Club.”We talk about the charm of Plantation Harbor Marina, our new paddleboard adventures, snorkeling with sea turtles, and eating our weight in tuna nachos at Marker 88. There's even a surprise iguana cameo and a spontaneous swim (unplanned, of course) by the captain himself.Plus, we preview what’s next on our Loop journey—from Key Largo to Fort Lauderdale—as we chase clear water, great reefs, and smoother sailing.

In this conversation, Chris and Deb share their recent adventures in the Florida Keys, focusing on their experiences with dinghy exploration, wildlife encounters, diving, local dining, and boat maintenance. They discuss the beauty of Boot Key Harbor, the importance of wildlife conservation, and their plans for future family visits. The conversation highlights the joys and challenges of life on the water, along with practical insights into boat insurance and maintenance.

In this conversation, Chris and Deb share their experiences at Marlin Bay Marina and their adventures in the Florida Keys. They discuss their travels, the unique aspects of Key West, and the challenges of living on a boat, including repairs and transportation. They also outline their future plans for exploring more of the Keys and potentially heading to the Bahamas.

In this episode, Chris and Deb share their exciting journey to Marathon in the Florida Keys, detailing their experiences with boat maintenance, navigating challenging waters, and their plans for exploration in the area. They discuss the importance of proper boat upkeep, the challenges faced during their trip, and the beauty of the Keys, all while sharing humorous anecdotes and insights from their adventure.

In this conversation, Chris and Deb share their recent boating adventures, detailing their journey from Pine Island to Naples and Marco Island. They discuss the challenges and joys of cruising, including navigating under fixed bridges, enjoying local restaurants, and the importance of preparation when docking. They also recount a thrilling dinghy adventure and their plans for future travels to the Florida Keys, emphasizing the beauty of the locations and the camaraderie experienced along the way.

In this episode, Chris and Deb share their recent adventures aboard SeaDan after returning from repairs. They discuss their journey through the canals, experiences with locks, and the beauty of Cayo Costa. The couple also recounts their visits to Cabbage Key and North Captiva, highlighting the local cuisine and unique experiences. They face challenges with fuel and navigation but enjoy the stunning scenery and marine life along the way. The episode concludes with plans for future stops and activities.