Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.
Freestyle Travel Show
Claim This Podcastby Freestyle Travel Show
4.9(21 reviews)
132 episodes
Updated Weekly
Accepts GuestsHas SponsorsLocation 🇬🇧
69
Podcast Authority
BetaGoodBased on show quality, social media presence, reviews, charts, and more
Quality83
Social0
YouTube85
Engagement51
Podcast Overview
Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.
Language
🇺🇲
Publishing Since
4/16/2017
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69
Podcast Authority
BetaGoodBased on show quality, social media presence, reviews, charts, and more
Quality83
Social0
YouTube85
Engagement51
8
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10
Growth Opportunities
excellent
Episode Length
44 minutes
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good
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3.0/5
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Recent Episodes
June 21, 2026
#132 - Hitchhiking from North Carolina to Colorado
<p>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.</p><p>Join in on Kenny's app, use travel tools, and meet other travelers: <a href="https://www.triphopping.com/" target="_blank">https://www.triphopping.com</a></p><p>Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: <a href="https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform" target="_blank">https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform</a></p><p>====</p><p>Support the show and Kenny's other projects while getting some bonuses here: <a href="https://www.patreon.com/kennyflannery" target="_blank">https://www.patreon.com/kennyflannery</a></p><p>Kenny's written two books available on Amazon in paperback, eBook and audiobook:</p><p>"A Six-Pack of Hitchhiking Stories": <a href="https://amzn.to/2IynlFm" target="_blank">https://amzn.to/2IynlFm</a></p><p>"Nomadic Moonlight": <a href="https://amzn.to/40NjWc4" target="_blank">https://amzn.to/40NjWc4</a></p><p>Kenny designed the transforming BivyPack and recommends third-party travel gear at <a href="http://www.freestyletravelgear.com/" target="_blank">http://www.FreestyleTravelGear.com</a></p><p>Hopping YouTube Channel (Kenny's travel/beer series): <a href="https://www.youtube.com/Hopping" target="_blank">https://www.youtube.com/Hopping</a></p><p>== FOLLOW KENNY FLANNERY ==</p><p>@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and <a href="http://www.hobolifestyle.com/" target="_blank">http://www.hobolifestyle.com</a></p><p>Sign up for Kenny's free newsletters: <a href="https://mailchi.mp/73c728259c7a/kennyflannery" target="_blank">https://mailchi.mp/73c728259c7a/kennyflannery</a></p><p>== KENNY'S TRAVEL PROMO CODES ==</p><p>- Get 30% off your TrustedHousesitters membership: <a href="https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend" target="_blank">https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend</a></p><p>- Get a $20 credit on Airbnb: <a href="http://www.airbnb.com/c/kflannery16?s=8" target="_blank">http://www.airbnb.com/c/kflannery16?s=8</a> </p><p>- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE</p><p>- Free ride on uber: uberhobolifestyle </p><p>- Get fabric and materials from the same place I do to make my BivyPacks: <a href="https://ripstopbytheroll.com/?rfsn=6483074.61c931" target="_blank">https://ripstopbytheroll.com/?rfsn=6483074.61c931</a></p><p>You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out <a href="http://www.freestyletravelshow.com/" target="_blank">http://www.freestyletravelshow.com</a>.</p><p><a href="https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428" target="_blank">https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428</a></p><p><a href="http://www.twitter.com/freetravelshow" target="_blank">http://www.twitter.com/freetravelshow</a></p><p><a href="http://www.facebook.com/freestyletravelshow" target="_blank">http://www.facebook.com/freestyletravelshow</a></p><p>RSS Feed: <a href="https://anchor.fm/s/ddb5efa4/podcast/rss" target="_blank">https://anchor.fm/s/ddb5efa4/podcast/rss</a></p><p>Want to support the show? You can cashapp $kenflannery or venmo @kenflannery</p><p>Thanks!</p><p>Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.</p>
May 7, 2026
#131 - On The Road With Christian Cronin
<p>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.</p><p>Join in on Kenny's app, use travel tools, and meet other travelers: <a href="https://www.triphopping.com/" target="_blank">https://www.triphopping.com</a></p><p>Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: <a href="https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform" target="_blank">https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform</a></p><p>====</p><p>Support the show and Kenny's other projects while getting some bonuses here: <a href="https://www.patreon.com/kennyflannery" target="_blank">https://www.patreon.com/kennyflannery</a></p><p>Kenny's written two books available on Amazon in paperback, eBook and audiobook:</p><p>"A Six-Pack of Hitchhiking Stories": <a href="https://amzn.to/2IynlFm" target="_blank">https://amzn.to/2IynlFm</a></p><p>"Nomadic Moonlight": <a href="https://amzn.to/40NjWc4" target="_blank">https://amzn.to/40NjWc4</a></p><p>Kenny designed the transforming BivyPack and recommends third-party travel gear at <a href="http://www.freestyletravelgear.com/" target="_blank">http://www.FreestyleTravelGear.com</a></p><p>Hopping YouTube Channel (Kenny's travel/beer series): <a href="https://www.youtube.com/Hopping" target="_blank">https://www.youtube.com/Hopping</a></p><p>== FOLLOW KENNY FLANNERY ==</p><p>@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and <a href="http://www.hobolifestyle.com/" target="_blank">http://www.hobolifestyle.com</a></p><p>Sign up for Kenny's free newsletters: <a href="https://mailchi.mp/73c728259c7a/kennyflannery" target="_blank">https://mailchi.mp/73c728259c7a/kennyflannery</a></p><p>== KENNY'S TRAVEL PROMO CODES ==</p><p>- Get 30% off your TrustedHousesitters membership: <a href="https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend" target="_blank">https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend</a></p><p>- Get a $20 credit on Airbnb: <a href="http://www.airbnb.com/c/kflannery16?s=8" target="_blank">http://www.airbnb.com/c/kflannery16?s=8</a> </p><p>- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE</p><p>- Free ride on uber: uberhobolifestyle </p><p>- Get fabric and materials from the same place I do to make my BivyPacks: <a href="https://ripstopbytheroll.com/?rfsn=6483074.61c931" target="_blank">https://ripstopbytheroll.com/?rfsn=6483074.61c931</a></p><p>You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out <a href="http://www.freestyletravelshow.com/" target="_blank">http://www.freestyletravelshow.com</a>.</p><p><a href="https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428" target="_blank">https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428</a></p><p><a href="http://www.twitter.com/freetravelshow" target="_blank">http://www.twitter.com/freetravelshow</a></p><p><a href="http://www.facebook.com/freestyletravelshow" target="_blank">http://www.facebook.com/freestyletravelshow</a></p><p>RSS Feed: <a href="https://anchor.fm/s/ddb5efa4/podcast/rss" target="_blank">https://anchor.fm/s/ddb5efa4/podcast/rss</a></p><p>Want to support the show? You can cashapp $kenflannery or venmo @kenflannery</p><p>Thanks!</p><p>Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.</p>
March 29, 2026
#130 - Journey North From the Bottom of South America
<p>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.</p><p>Join in on Kenny's app, use travel tools, and meet other travelers: <a href="https://www.triphopping.com/" target="_blank">https://www.triphopping.com</a></p><p>Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: <a href="https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform" target="_blank">https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform</a></p><p>====</p><p>Support the show and Kenny's other projects while getting some bonuses here: <a href="https://www.patreon.com/kennyflannery" target="_blank">https://www.patreon.com/kennyflannery</a></p><p>Kenny's written two books available on Amazon in paperback, eBook and audiobook:</p><p>"A Six-Pack of Hitchhiking Stories": <a href="https://amzn.to/2IynlFm" target="_blank">https://amzn.to/2IynlFm</a></p><p>"Nomadic Moonlight": <a href="https://amzn.to/40NjWc4" target="_blank">https://amzn.to/40NjWc4</a></p><p>Kenny designed the transforming BivyPack and recommends third-party travel gear at <a href="http://www.freestyletravelgear.com/" target="_blank">http://www.FreestyleTravelGear.com</a></p><p>Hopping YouTube Channel (Kenny's travel/beer series): <a href="https://www.youtube.com/Hopping" target="_blank">https://www.youtube.com/Hopping</a></p><p>== FOLLOW KENNY FLANNERY ==</p><p>@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and <a href="http://www.hobolifestyle.com/" target="_blank">http://www.hobolifestyle.com</a></p><p>Sign up for Kenny's free newsletters: <a href="https://mailchi.mp/73c728259c7a/kennyflannery" target="_blank">https://mailchi.mp/73c728259c7a/kennyflannery</a></p><p>== KENNY'S TRAVEL PROMO CODES ==</p><p>- Get 30% off your TrustedHousesitters membership: <a href="https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend" target="_blank">https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend</a></p><p>- Get a $20 credit on Airbnb: <a href="http://www.airbnb.com/c/kflannery16?s=8" target="_blank">http://www.airbnb.com/c/kflannery16?s=8</a> </p><p>- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE</p><p>- Free ride on uber: uberhobolifestyle </p><p>- Get fabric and materials from the same place I do to make my BivyPacks: <a href="https://ripstopbytheroll.com/?rfsn=6483074.61c931" target="_blank">https://ripstopbytheroll.com/?rfsn=6483074.61c931</a></p><p>You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out <a href="http://www.freestyletravelshow.com/" target="_blank">http://www.freestyletravelshow.com</a>.</p><p><a href="https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428" target="_blank">https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428</a></p><p><a href="http://www.twitter.com/freetravelshow" target="_blank">http://www.twitter.com/freetravelshow</a></p><p><a href="http://www.facebook.com/freestyletravelshow" target="_blank">http://www.facebook.com/freestyletravelshow</a></p><p>RSS Feed: <a href="https://anchor.fm/s/ddb5efa4/podcast/rss" target="_blank">https://anchor.fm/s/ddb5efa4/podcast/rss</a></p><p>Want to support the show? You can cashapp $kenflannery or venmo @kenflannery</p><p>Thanks!</p><p>Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.</p>
132 total episodes available
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