PODCAST · society
Freestyle Travel Show
by Freestyle Travel Show
Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.
Episodes
-
#133 - Stories Hitchhiking in the West
Starting his 20th year on the road, Kenny hitchhikes from Colorado to Wyoming, then takes a gamble through Nevada to Arizona. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com ==== Support the show and Kenny's other projects while getting some bonuses...
-
#132 - Hitchhiking from North Carolina to Colorado
Kenny hitchhikes from North Carolina to Colorado via Indiana, Michigan, Minnesota, Iowa, and Kansas City. Catch up with friends, stealth camp, deal with police, drink some beers, and take the ride. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com...
-
#131 - On The Road With Christian Cronin
Kenny talks to a friend and previous guest, Christian Cronin, as they cruise out of Mississippi on a little road trip. After, Kenny catches you up getting from Peru to Florida, a casino fail, doing bike deliveries, and hitchhiking to Mississippi to make his latest backpack. Join in on Kenny's…
more -
#130 - Journey North From the Bottom of South America
After reaching the bottom of South America, Kenny turns around and starts hitching north via the east. A long desert truck ride through Argentina to Buenos Aries, through Uruguay, into Brazil, epic waterfalls, Paraguay, sketchy dirt road hitchhiking in Bolivia, and eventually to Cusco, Peru. Join...
-
#129 - The End of The Road in South America
Kenny hitchhikes from Peru to the end of the road in Tierra del Fuego, the bottom of South America. Camping, getting a phone stolen, meeting other travelers, and insane beauty line the road down. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com…
more -
#128 - End of Year USA Zig Zag
Kenny travels thousands of miles from Arizona to Texas, to the East Coast, south to Florida, across to Wyoming, south through Utah and Vegas, back to Arizona, and again back to Texas. New friends, old friends, family, random generosity, casino wins, trucks, and other madness set up an impending...
-
#127 - Trip Hopping in Arizona
Kenny hitchhikes to Arizona for another Trip Hopping collective. Besides releasing the iOS app and other improvements, some little van trips up to Northern Arizona prove to be good times as well. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com…
more -
#126 - Booted From Nevada To California
Kenny hitches from Wyoming to Salt Lake to see a friend, to Reno to get kicked out of a casino, to Sacramento and Chico to see more friends, and south to LA and San Diego. Inching closer to Phoenix for the Trip Hopping collective, things are working out. Join in on Kenny's app, use travel tools,...
-
#125 - Trip Hopping Invite & Western Hitchhike
Kenny puts out an invite to the upcoming Trip Hopping collective and talks about hitchhiking from the Midwest to Montana and Wyoming. Reach out if you're interested in coming to Arizona this October for the collective to be a part of all things Trip Hopping. Join in on Kenny's app, use travel...
-
#124 - Liz Stewart in Sioux City
Liz Stewart strikes again, thriving in Sioux City. Kenny hitches to Iowa to catch up with her in her downtown studio space to hear what she's been up to. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com Really interested? Check out the volunteer form...
-
#123 - Midwest Hitchhiking
Hitchhiking through the Midwest from Nashville, to Indy, up through Michigan and down to Wisconsin and Iowa. Kenny catches up with friends, meets plenty of people on the road, and is sure to have a beer or two every step of the way. Join in on Kenny's app, use travel tools, and meet other...
-
#122 - From New York to Nashville
Kenny flies from Greece to New York City and begins tripping on down the east coast before turning westbound. Catch up with old friends and family, get some interesting rides hitchhiking, and take advantage of a housesitting site in another freestyle adventure. Join in on Kenny's app, use travel...
-
#121 - Journey from Portugal to Greece
Hitchhiking from Portugal 4,200+ kilometers over 11 days, catching 59 rides dealing with police in multiple countries, getting soaked, sleeping everywhere, and all for a cheap plane ticket. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com Really...
-
#120 - Hitchhiking from Holland to Spain
Kenny hitchhikes 2,500+ kilometers in one stretch from Holland to the south of Spain. The four day journey involves the Eiffel Tower at midnight, stealth camping, navigating the rain, being taken in by a couple armed with local wine & congac from the region, driving a van for 1,000 kilometers…
more -
#119 - To The Netherlands
After England, Kenny uses a budget airline to skip to Germany, where hitchhiking to Amsterdam is easy. Good times there lead to another short hitch to see another old friend, also in The Netherlands. You have a limited offer you can use now for Magic Mind, that gets you up to 48% off your first...
-
#118 - Quick Trip Through England
Over in England, Kenny hitchhikes to Poole to help a friend with her project, then makes his way up to Liverpool before planning his escape from the UK. You have a limited offer you can use now for Magic Mind, that gets you up to 48% off your first subscription or 20% off one-time purchases with...
-
#117 - Police Thumb Down My Nevada Desert Run To England
A surprise trip to England required hitchhiking through the desert to Las Vegas to catch a flight, but the police complicate the matter and Kenny is cutting it close. Plus some Trip Hopping updates. Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com...
-
#116 - Hitchhiking Through the Desert From California to Phoenix via Nevada
Kenny hitchhikes out of the worst place in the world (for hitchhiking, Los Angeles) to San Diego to see some friends. Afterward, he hitchhikes into the desert via long lonely roads in a roundabout way to Phoenix to get cracking on the Trip Hopping app. Join in on Kenny's app, use travel tools…
more -
#115 - Hitchhiking Down California
Kenny hitchhikes to the north of California and all the way down to Los Angeles. Along the way he sees friends, family, meets some new people and wakes up sliding down hills. To try out the Trip Hopping Android app, you can request to join this group for a link:...
-
#114 - Revisiting People and Places
2025 has begun traveling from Wyoming to Salt Lake City, Reno, and California. Kenny talks about some interesting rides and reflects on what it's like revisiting people and places over a nearly 18-year span of living out of a backpack around the world. To try out the Trip Hopping Android app, you...
-
#113 - 2024 Hitchhiking Stats and Travel Recap
Kenny compiles the hitchhiking statistics from 2024 and recaps a year of traveling through 34 countries. It was a great year, give a listen to hear how many days he hitchhiked, how many rides he got, how far he traveled, and some of the stories along the way. To try out the Trip Hopping Android...
-
#112 - Hitchhiking From North Carolina to Arizona Was Awesome
Kenny hitchhikes from North Carolina to Arizona. A few friends are on the path, some state troopers offer some rides, and some very interesting people help keep the trip moving along. To try out the Trip Hopping Android app, you can request to join this group for a link:...
-
#111 - Back in the States
Kenny is back in the USA and hitchhiking from Pennsylvania to Atlantic City for the first time, then through Delaware to Virginia and North Carolina. Gambling, breweries, new friends and family all on the path. To try out the Trip Hopping Android app, you can request to join this group for a…
more -
#110 - Iceland is Beautiful Until Airport Trouble
A transit trip through Iceland proves very beautiful during a week of hitchhiking around the island, but gets ugly at the airport when Kenny's pulled off the plane and delayed for a day dealing with security and police. To try out the Trip Hopping Android app, you can request to join this group…
more -
#109 - Hitchhiking in The Balkans
Hitchhiking from Turkey to the Balkans involves a high-speed police chase while hitchhiking, making the news in Kosovo, beautiful hiking, escaping before the police arrive again, and generally meeting friendly people along the route. To try out the Trip Hopping Android app, you can request to…
more -
#108 - Turkey Treats Me Well
Kenny hitchhikes the border from Armenia to Georgia and into Turkey, experiencing generosity, police, and a lot of steep camping. To try out the Trip Hopping Android app, you can request to join this group for a link: https://groups.google.com/g/trip-hopping-testers Really interested? Check out…
more -
#107 - Beat By a Rabbit in Armenia
Kenny gets punked by a Rabbit his first day in Armenia, but has some great hospitality before and after that makes up for it. Trip over the border from Georgia and experience the journey. To try out the Trip Hopping Android app, you can request to join this group for a link:...
-
#106 - Trip Hopping is Getting Better
Trip Hopping has improved significantly, Kenny's travel app aids in linking up with people while you travel to Explore, Stay, and Go where you want... it's fun! Kenny talks about the latest updates you can use right now, what's coming, and how it's been going in Georgia. Also, there's a Brew a...
-
#105 - Hitching across Turkey
Hitchhiking across Turkey, Kenny encounters friendly people and sees some interesting sights on his way to Georgia. There have been some more Trip-Hopping developments, and the good times continue. https://www.triphopping.com Get your Magic Mind subscription here:...
-
#104 - Trip Hopping is Live
Trip Hopping is Kenny's app designed to share our travels. Now open for all to join, Kenny talks about its best features, like "going live" to connect with other travelers, search for transportation and accommodation, and share your trips and notes with friends. https://www.triphopping.com Get…
more -
#103 - Finland to Poland
Kenny hitchhikes the last bit of Finland, ferries down to Estonia and hitchhikes to Latvia to be an English language coach with an old friend before hitching further through Lithuania and Poland, staged for the next adventure. Try Magic Mind for free here: https://magicmind.com/FREESTYLESHOWTRIAL...
-
#102 - Norway is Legit
Kenny finally gets to Norway and the infinite sunlight that levels up his hitchhiking. Take the trip from the Netherlands and Belgium through Germany to Denmark, Sweden, Norway, and Finland. For Magic Mind you have a limited offer you can use now, that gets you up to 48% off your first…
more -
#101 - Walter Heck is Awesome
Walter has been Kenny's friend since meeting in Alaska traveling and have crossed paths around the world whenever possible, and this is yet another one of those glorious times. After the beers, conversations, and whiskey chats about travel, Kenny gives an update on his recent travels as well as…
more -
#100 - Italy to Germany
One hundred episodes, woot! This one has planes, trains, buses, hitchhiking and plenty of walking as Kenny arrives in Italy and makes his way through the south and gradually up through Switzerland, Prague and Germany. ==== Support the show and Kenny's other projects while getting some bonuses…
more -
#99 - In Ireland Again
A third time in Ireland has Kenny hitchhiking, helping friends with the Yoga Mandala Project, finding a leprechaun in Kilkenny and running into friends from the States. ==== Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery Kenny's...
-
#98 - Random Tahoe Trip Before Ireland
A short hitchhiking ride becomes a long ride and unexpected trip to a record-breaking blizzard in Tahoe full of good times, and propels Kenny to New York City, London, and ultimately Ireland for another great adventure ahead. ==== Support the show and Kenny's other projects while getting some...
-
#97 - Trip Hopping Preview
Trip Hopping isn't here yet, but Kenny wants to share a little preview of what it's all about and potentially how you can get involved. A kick-ass travel app is coming, and here's what you can expect. Go to https://www.magicmind.com/JANfreestyletravel for 1 month free when subscribing for 3…
more -
#96 - Hitchhike with me to Phoenix
Live hitchhiking! I recorded this episode through the day hitchhiking from Laughlin in Nevada to Phoenix in Arizona. Listen to every step of the way as I navigate my way there using my feet and my thumb. Go to https://www.magicmind.com/JANfreestyletravel for 1 month free when subscribing for 3...
-
#95 - Hitchhiking to Vegas
After catching up with family in Wyoming, Kenny revisits some Hopping breweries and hitchhikes his way to Vegas on an awesome day coming from seeing friends in Salt Lake City. Vegas shenanigans ensure, talk of a coming travel app, and good times ahead. Go to...
-
#94 - Hitchhiking a Tesla
Kenny hitchhikes from Mississippi to North Carolina and gets the longest ride in a Tesla he's gotten so far. More tripping around from there, including a cold night heading towards Florida, state police interrupting the day, and getting all the way out to Wyoming. Go to...
-
#93 - David in New Orleans
David is back on the show, this time in New Orleans to talk about his travels the past few years and what he's been getting into. Kenny talks about getting from San Diego to New Orleans and good times on Halloween. Go to https://www.magicmind.com/freestyletravel and get 56% off your subscription...
-
#92 - Sean
Sean is one of Kenny's childhood friends and was his roommate just before Kenny started his life on the road. The two talk travel and philosophy while catching up on good times around San Diego.====Support the show and Kenny's other projects while getting some bonuses here:...
-
#91 - Planes, Trains, and Hitchhiking
This past month Kenny's been on trains, planes, hitchhiking, buses and staying everywhere from fancy hotels to friend's places and camping off the side of the road. This episode takes you through the midwest starting in Chicago on down through the likes of Saint Louis, Indianapolis, Michigan and...
-
#90 - Robert Struggles
Robert Struggles makes his debut on the Freestyle Travel Show, telling his story from meeting Kenny online while getting inspired to travel, to finally hitting the road and making some trips around the world. Afterwards, Kenny talks about hitchhiking through Iowa, Minnesota, and filming Hopping...
-
#89 - Liz Stewart in Iowa
Liz Stewart makes her fifth appearance on the show, this time in Iowa, where she's been living for nearly the past year as she's battled to stay clean with her presidential cat sidekick. Kenny hitchhiked on over from Wyoming to see her, film some Hopping episodes, and have a book signing while in...
-
#88 - Hitchhiking from Portland to Wyoming
Hitchhiking from Portland to Wyoming by way of Idaho with a fun drunk lady, happy days in Stanley, and Hopping in Teton Valley. ==== Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery Kenny's written two books available on Amazon in...
-
#87 - Hitchhiking to Portland
Hitchhiking to Portland from Southern California after also hitching to Arizona to see friends, popping through Vegas, and starting the brewery book tour. A fun summer begins. ==== Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery...
-
#86 - Hitching and Hiking to Southern California
In this episode, we hitchhike with Kenny from Northern California to Southern California. Slow hitchhiking days, fast days, an angry cop, free money, hiking to mountain tops, catching up with an old friend - all the things! ==== Support the show and Kenny's other projects while getting some…
more -
#85 - Hitchhiking to Chico
Hitchhiking from Arizona to Nevada and on towards Chico, California in this one. Also some news about the new book and what's been going on lately. ==== Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflannery Kenny's book "A Six-Pack of...
-
#84 - Tripping on Casino Comps
Hitched a ride with border patrol and tips on getting free rooms at casinos highlight this episode, where I take you on my trips from San Diego to LA, Nevada and a cabin in Arizona. Cheers! ==== Support the show and Kenny's other projects while getting some bonuses here:...
We're indexing this podcast's transcripts for the first time — this can take a minute or two. We'll show results as soon as they're ready.
No matches for "" in this podcast's transcripts.
TOPICS IN THIS SHOW
Loading reviews...
Loading similar podcasts...
Frequently Asked Questions
How many episodes does Freestyle Travel Show have?
Freestyle Travel Show currently has 133 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Freestyle Travel Show about?
Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.
How often does Freestyle Travel Show release new episodes?
Freestyle Travel Show publishes regularly with 133 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Freestyle Travel Show?
You can listen to Freestyle Travel Show 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 Freestyle Travel Show?
Freestyle Travel Show is created and hosted by Freestyle Travel Show.
URL copied to clipboard!