Episodios

  • #130 - Journey North From the Bottom of South America
    Mar 29 2026

    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.

    Más Menos
    51 m
  • #129 - The End of The Road in South America
    Feb 19 2026

    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.

    Más Menos
    40 m
  • #128 - End of Year USA Zig Zag
    Jan 20 2026

    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.

    Más Menos
    51 m
  • #127 - Trip Hopping in Arizona
    Nov 9 2025

    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.

    Más Menos
    25 m
  • #126 - Booted From Nevada To California
    Sep 28 2025

    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.

    Más Menos
    34 m
  • #125 - Trip Hopping Invite & Western Hitchhike
    Aug 23 2025

    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.

    Más Menos
    36 m
  • #124 - Liz Stewart in Sioux City
    Jul 21 2025

    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.

    Más Menos
    33 m
  • #123 - Midwest Hitchhiking
    Jul 18 2025

    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.

    Más Menos
    49 m