
Advertise on podcast: Freestyle Travel Show
Rating
4.9from
This podcast has
133 episodes
Language
EnglishPublisher
Freestyle Travel ShowExplicit
No
Date created
2017/04/23
Latest episode
2026/07/31
Average duration
45 min.
Release period
34 days
Description
Travel freely, spontaneously and indefinitely. These stories, interviews and discussions are tailor-made for hitchhikers, backpackers, couchsurfers and all who love to travel.
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#133 - Stories Hitchhiking in the West
2026/07/31
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 here: https://www.patreon.com/kennyflannery
Kenny's written two books available on Amazon in paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#132 - Hitchhiking from North Carolina to Colorado
2026/06/21
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
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#131 - On The Road With Christian Cronin
2026/05/07
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 app, use travel tools, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#130 - Journey North From the Bottom of South America
2026/03/29
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 in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#129 - The End of The Road in South America
2026/02/19
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
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#128 - End of Year USA Zig Zag
2026/01/20
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 visit back to Peru.
Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#127 - Trip Hopping in Arizona
2025/11/09
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
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#126 - Booted From Nevada To California
2025/09/28
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, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#125 - Trip Hopping Invite & Western Hitchhike
2025/08/23
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 tools, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#124 - Liz Stewart in Sioux City
2025/07/21
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 to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#123 - Midwest Hitchhiking
2025/07/18
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 travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#122 - From New York to Nashville
2025/06/19
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 tools, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#121 - Journey from Portugal to Greece
2025/05/20
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 interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#120 - Hitchhiking from Holland to Spain
2025/04/23
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, and all the good stuff that keeps Kenny on the road.
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 code
https://www.magicmind.com/FREESTYLELT at checkout
Join in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.com
Really interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform
====
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 paperback, eBook and audiobook:
"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm
"Nomadic Moonlight": https://amzn.to/40NjWc4
Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.com
Hopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping
== FOLLOW KENNY FLANNERY ==
@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.com
Sign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery
== KENNY'S TRAVEL PROMO CODES ==
- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend
- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8
- Get $20 off your Google Fi bill when you sign up with my code: TDW3EE
- Free ride on uber: uberhobolifestyle
- Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931
You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.
https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428
http://www.twitter.com/freetravelshow
http://www.facebook.com/freestyletravelshow
RSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rss
Want to support the show? You can cashapp $kenflannery or venmo @kenflannery
Thanks!
Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
#119 - To The Netherlands
2025/04/12
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 subscription or 20% off one-time purchases with codehttps://www.magicmind.com/FREESTYLELT at checkoutJoin in on Kenny's app, use travel tools, and meet other travelers: https://www.triphopping.comReally interested? Check out the volunteer form to help improve Trip Hopping in whatever way that you are uniquely qualified to do: https://docs.google.com/forms/d/e/1FAIpQLSfoi6e8v5yPTVbUZvEexWgymt6iqhl_1kZ1meYGSALpzBpddg/viewform====Support the show and Kenny's other projects while getting some bonuses here: https://www.patreon.com/kennyflanneryKenny's written two books available on Amazon in paperback, eBook and audiobook:"A Six-Pack of Hitchhiking Stories": https://amzn.to/2IynlFm"Nomadic Moonlight": https://amzn.to/40NjWc4Kenny designed the transforming BivyPack and recommends third-party travel gear at http://www.FreestyleTravelGear.comHopping YouTube Channel (Kenny's travel/beer series): https://www.youtube.com/Hopping== FOLLOW KENNY FLANNERY ==@HoboLifestyle on Twitter, Instagram, Facebook, YouTube and http://www.hobolifestyle.comSign up for Kenny's free newsletters: https://mailchi.mp/73c728259c7a/kennyflannery== KENNY'S TRAVEL PROMO CODES ==- Get 30% off your TrustedHousesitters membership: https://www.trustedhousesitters.com/refer/RAF611064/?utm_source=copy-link&utm_medium=refer-a-friend&utm_campaign=refer-a-friend- Get a $20 credit on Airbnb: http://www.airbnb.com/c/kflannery16?s=8 - Get $20 off your Google Fi bill when you sign up with my code: TDW3EE- Free ride on uber: uberhobolifestyle - Get fabric and materials from the same place I do to make my BivyPacks: https://ripstopbytheroll.com/?rfsn=6483074.61c931You can freely download or subscribe to this show in many ways and everywhere podcasts can be found, check out http://www.freestyletravelshow.com.https://itunes.apple.com/us/podcast/freestyle-travel-show/id1229479428http://www.twitter.com/freetravelshowhttp://www.facebook.com/freestyletravelshowRSS Feed: https://anchor.fm/s/ddb5efa4/podcast/rssWant to support the show? You can cashapp $kenflannery or venmo @kenflanneryThanks!Music in this episode is "Cali" performed by Cyderobin, written by Mark Tubridy.
Podcast reviews
Read Freestyle Travel Show podcast reviews
billy t franklin 2021/10/06
Egypt
The Egypt episode where Kenny was held captive for six days is pretty riveting. Just couldn't imagine.
ThroatPunchPros 2019/09/23
Awesome stories, hell of a dude
Picked this dude up walking outta Asheville NC and got the opportunity to listen to some stories as we rode for an hour or so. Had a few laughs, and e...
Miles P183721 2018/06/15
Hitchhiking in all the places
Great show. Definitely makes me want to hitchhike everywhere. I love his stories about the random people who give Kenny rides. He gets offered joints ...
Ineedanickname2 2017/05/18
Great tips and stories
Listening in you'll find the thinking and courage it takes to live free. Kenny Flannery has interesting perspectives and stories that make you reconsi...
zpb14 2017/05/03
Great show
Very interesting and great to listen to when you're in the mood for awesome new things!
PDXmusicman2000 2017/05/03
Great show!
Great first few episodes! Can't wait to hear some of the wacky travel stories and interviews.
jazgm212 2017/05/02
Fun and informative!
Sometimes you just need to listen to something that makes you smile and lol. Something that lets you escape your everyday routine, especially when you...
StephersPDX 2017/05/02
Travel tips & stories
On his show, Kenny shares his knowledge and experiences from hitchhiking, couch surfing and exploring the world in his freestyle approach. His experie...
JuBut 2017/05/01
Freestyle Travel Show
Fascinating to hear how this young man has crafted and carved out a life of endless adventures, with seemingly no means of financial support except th...
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