Freestyle Travel Show

Freestyle Travel Show

Society EN ↓ 132 episodes

Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.

Author

Freestyle Travel Show

Category

Society

Podcast website

www.freestyletravelshow.com

Latest episode

Jun 21, 2026

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Episodes

#82 - New BivyPack, House-sitting, and Hitchhiking 28.11.2022

A new BivyPack, a look at TrustedHousesitters, and hitchhiking stories are highlighted in this latest episode, recorded in North Carolina. As mentioned in the episode, here's my referral code for TrustedHousesitters: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend ==== Support the show and Kenny's other projects while...

#81 - Tys Sniffen & Backpacks 16.09.2022

Tys Sniffen makes an innovative travel backpack. He shows it off and he and Kenny compare bag styles and travel philosophy, while also discussing Trustroots and travel hospitality networks. Afterward, Kenny catches you up his coastal hitchhiking in California and beyond, as well as plans for his new backpack design. Use promo code FREESTYLETRAVEL at ideamountain.com to save 15% on the backpack tha...

#80 - Zane Lamprey 04.08.2022

Zane Lamprey is a standup comedian known for his shows like "Drinking Made Easy" where he travels and drinks. Sound familiar? That's why he's on the show. I catch up with him backstage in Reno before his show, then tell the story of hitchhiking here. https://www.zanelamprey.com https://pleepleus.com ==== Support the show and Kenny's other projects while getting some bonuses here: https://www.patre...

#79 - Hitchhiking Near Mountains is Easy 06.07.2022

Typical Vegas nonsense is followed by a fishing trip in Idaho and hitchhiking around Jackson Hole, Wyoming. ==== 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 Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designed the transforming B...

#78 - Hitchhiking from Louisiana to Nevada 04.06.2022

Kenny hitchhikes from Louisiana to Nevada, by way of Dallas, Carlsbad, and a beer-filled good time in Phoenix. ==== 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 Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designed the transformin...

#77 - Free Cruise and Mississippi Booze 04.05.2022

A free Caribbean cruise, the release of the Hopping beer/travel show, and a spontaneous mission to hit every Mississippi brewery in under 24 hours lead Kenny to yet another free casino stay near Shreveport, Louisiana. ==== 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 Hitchhiking Stories" is available...

#76 - Hitchhiking through Texas to New Orleans 10.04.2022

Kenny is in New Orleans after hitchhiking around Texas to Austin for South By Southwest and other kicks, a night in Houston, and a good long day hitching to Louisiana. The cruise is coming up, and excitement is building. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designed th...

#75 - Liz is Clean 06.03.2022

Liz Stewart returns to the podcast, now clean while living and working in rural Texas on a beautiful property that hosts luxury events like weddings and culinary experiences. Kenny hitched on out to pay her a visit and hear her most recent stories of beating addiction. Afterwards you get a little catch up on Kenny's travels from New York to Nevada, driving an RV from South Dakota, and what's up ne...

#74 - Couchers.org with Itsi Weinstock 05.02.2022

Couchers.org came about after Couchsurfing.com put up its paywall in 2020, leaving many hosts and travelers looking for an alternative. Itsi Weinstock, one of Couchers' co-founders, sits down with Kenny to talk about their mission, how far they've come, and what's in store for the hospitality network. After their discussion, Kenny catches you up on his travels from Vermont, to NYC, and on to Vegas...

#73 - Matt Stove 26.01.2022

Matt Stove was on the road for years, hitchhiking all over the world, and now he's in the position to give travelers a little slice of heaven here in Vermont. Kenny then catches you up on the past couple of months of his travels, which involves a ridiculous Vegas run. To contact Matt, visit https://sliceofheaven.us/ == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is availab...

#72 - Hitchhiking, Planes, Gambling and Weed 19.11.2021

Gambling, hitchhiking, stealth camping, fancy hotels, old friends, trains, planes, Vegas, poker, and heaps or marijuana are packed into this past month. Enjoy! == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designed the transforming BivyPack and recommends third-party travel gea...

#71 - Four Casinos and a Wedding 06.10.2021

Over the past month, I've covered thousands of miles hitching rides with 18-wheelers and other drivers while bouncing between four casinos offering me comped rooms, and also celebrating at a family wedding. It's been a trip. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designe...

#70 - Molly Jo! 27.08.2021

Molly is a legend, a traveler, and a friend of Kenny's that's hitchhiked around the world, hiked for months on end, and partied without any stopping in sight. They recount their stories of meeting and early travels, then Kenny catches you up on the marijuana ranch he's landed in. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and...

#69 - The Hopping Saga 15.07.2021

Season 2 of Hopping had Kenny hitchhiking from Denver to Portland to visit amazing craft breweries, enjoy the spoils of the road, and deal with more drama than he bargained for. The episodes won't be released for several months, but you can hear Kenny tell about the adventure here, as well as what he's been getting into since wrapping up filming. If you haven't watched Season 1, you can do so for...

#68 - Hopping and Dogsitting 29.04.2021

Hopping is Kenny's show all about beer and backpacking, and the start of filming is just a month away. Before May 5, 2021 you can still back the project on Kickstarter: https://www.kickstarter.com/projects/kennyflannery/hopping-the-backpacking-beer-adventure-continues?ref=erkua6 Kenny also catches you up on the past month of dog sitting and running into friends as he gets ready for the big beer sh...

#67 - Beer Travel in Florida 25.03.2021

Getting back into Florida Kenny decided to do even more walking and brewery visiting than usual. All told, he went to 75 different Florida breweries after the latest trip from Key West to the panhandle. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designed the transforming Biv...

#66 - How I Got To The Bahamas 18.02.2021

The best part of freestyle travel is leaving yourself open to spontaneous opportunities. Just such a thing happened while hitchhiking around Florida, visiting a great brewery, and sending an off-hand "how's it been" text to an old friend. This episode gets into Kenny's hitching out of Saint Petersburg, Florida, meeting a string of interesting people, spending a day sailing, and ultimately winding...

#65 - How to Start Traveling 04.02.2021

Long-term and even indefinite travel is easier than most people think. I'll break down travel rhythms & styles, how to break away, what it's like day-to-day, and how the money works. I'll also catch you up on my travels since Kansas City to here in Florida and what's been happening here. Link to a blog post on the same topic: https://www.hobolifestyle.com/2021/01/how-to-start-traveling-indefinitel...

#64 - Liz Stewart in Kansas City 10.01.2021

Liz Stewart returns to the podcast to tell the next chapter in her journey, as Kenny catches up with her in Kansas City to start 2021. From her past two appearances you've heard how she organized the March for Marijuana in Alabama, then bailed on it and disappeared, got caught up in addiction leading to burning out in New Mexico before finally recovering. In this episode, you'll learn that recover...

#63 - Who Picks Up Hitchhikers and 2020 Statistics 25.12.2020

There are certain reoccurring "types" of people who pick up hitchhikers. Kenny breaks down some of these types using examples from his latest journey from North Carolina to Wyoming. Also, he lays out his hitchhiking statistics from the year 2020. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to...

#62 - Minimal Travel Packing with Video Gear 20.11.2020

Chatting about all the gear to pack while traveling while keeping your backpack under fifteen pounds (or at least as light as possible). There's a focus on cameras, microphones, drones, and other minimal gear you can pack to create videos and podcasts without weighing yourself down. Kenny also talks about the hurricane in Mississippi and wet hitchhiking from Florida to North Carolina. Packing vide...

#61 - Nick Noyes and Hopping 14.10.2020

Nick Noyes and I filmed "Hopping: The backpacking beer adventure" back in January and released episodes on YouTube this past summer. We crack some beers and talk about the adventure, the upcoming second season, and whatever else comes to mind. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2I...

#60 - Mystery Solved Hitchhiking to Midwest 14.09.2020

After a mysterious disappearance of gear, Kenny hits the road and covers many miles and states hitchhiking, and miraculously gets some closure on that mystery. Follow his rambling journey from Montana to Idaho and eventually to Minnesota by way of friends and new friends and plenty of good times. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in pape...

#59 - Montana Sake Blackout Mystery 08.08.2020

Waking up in a yard in Montana, unsure how I got there, and later unsure where some of my stuff had gone to. I unwrap that mystery and police involvement. All that after talking about hitchhiking through Glacier National Park and more of beautiful Montana. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https...

#58 - Hitchhiking in Montana 01.08.2020

Hitchhiking around Montana has proven beautiful. Kenny talks about dumb mistakes, great rides, stealth camping, brewery visits, and what's going on in Montana. == Kenny's projects == Kenny's book "A Six-Pack of Hitchhiking Stories" is available on Amazon in paperback, eBook and audiobook formats: https://amzn.to/2IynlFm Kenny designed the transforming BivyPack and recommends third-party travel gea...

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