Skip to content
CHAPTER 417 Ft. Charley Boorman episode artwork

EPISODE · Aug 14, 2026 · 3H 15M

CHAPTER 417 Ft. Charley Boorman

from Gypsy Tales

Charley Boorman sits down with Jase to tell the real story behind Long Way Round, the trip with Ewan McGregor that changed the motorcycle adventure genre forever. From how the idea came together over dinner in London, to the Dakar Rally training that got him ready, to riding the Road of Bones across Siberia to Magadan, Charley walks through the trip that shaped his life. They get into what four months on the road with Ewan actually taught him, how the Sky One deal came together, the Long Way Down and Long Way Up follow-ups, riding Australia end to end, 53 miles of hard enduro at the Isle of Man with David Knight, and what makes Jett Lawrence and Marc Marquez operate on a different level than the rest of us. Whether you've watched every Long Way series or you're finding Charley for the first time, this is the interview that goes deeper than the shows ever could. Watch on YouTube: https://www.youtube.com/watch?v=OS_mpK0lzxg Listen on Spotify/Apple → https://pod.link/1335551721 🎧 SHOP THE CARDO PACKTALK EDGE: https://cardosystems.com/collections/off-road 🛒 SHOP THE CARDO VENTURE HELMET: https://cardosystems.com/pages/venture 🏍 MOTOSPORT.COM: https://www.motosport.com/?rstr=62946&ls=8vu&utm_source=roster&utm_medium=influencer&utm_campaign=-jasonmacalpine-62946 🧤 FIST HANDWEAR: http://www.fisthandwear.com CODE: GYPSYGANG for 15% off 💧 Order SOTA Fuel "Gypsy Juice" https://sotafuel.com/products/sota-fuel-hydration-30-pack?variant=42103959945258 Timestamps: 0:00 Intro 1:54 Welcome Charley Boorman to Gypsy Tales 2:26 Jase on the Subscribe Discovery 4:57 Meeting Charley at the Isle of Man TT 10:16 The David Jeffries Story 14:40 Cardo Systems Ad 22:01 Riding Australia End to End 25:49 Living in Queensland with Jason Connery's Mother 34:57 Racing the Dakar Rally 37:07 The Race to Dakar Documentary 40:04 What It Takes to Make the Dakar 50:54 Coming Back to Dakar 52:13 Jumping Into Long Way Down 54:37 The Real Story Behind Long Way Round 1:03:47 Getting the Sky One Deal 1:07:06 Motosport Ad 1:13:54 Collecting Dream Motorcycles 1:24:05 Why Ewan Wanted to Do the Trip 1:30:04 Riding Into Russia 1:38:38 Jase's Scottish Roots 1:39:33 Through Mongolia 1:41:12 The Road of Bones to Magadan 1:45:51 Magadan to Anchorage 1:51:05 Long Way Round 1:58:19 How Long Way Round Inspired So Many 2:04:27 Fist Handwear Ad 2:07:51 The Making of Long Way Down 2:12:58 Africa in All Its Vibrance 2:19:04 The Dangers of Border Crossings 2:32:29 Charley's Dream Australian Ride 2:36:56 Ducati's Desert X 2:37:38 The Bike Charley Bought Himself 2:42:41 53 Miles of Hard Enduro at the Isle of Man with David Knight 2:47:04 What Makes Elite Riders Different 2:47:40 Sota Fuel Ad 2:48:28 Why Jett Lawrence Is So Good 2:51:43 How Soccer Players Handle Injuries vs MotoGP 3:00:58 Charley's Bucket List Rides 3:07:38 The European Bucket List Tour 3:14:02 Closing 📸 FOLLOW GYPSY TALES ON INSTAGRAM: @gypsytalespodcast 🛒 Shop Gypsy Tales merch: https://gypsytales.com 💼 Business inquiries: [email protected] See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episode metadata supplied by the publisher feed · Published Aug 14, 2026

Embed this episode

Ready to play

CHAPTER 417 Ft. Charley Boorman

0:00 3:15:31

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

Asian Wander Women Podcast Ivy Xu and Emily Fang Join your travel besties Emily and Ivy on their exciting journeys designing unconventional lives of location independence and blazing their own career paths.After meeting in San Francisco in their early 20s, the duo have quit jobs, started remote businesses, worked as ex-pats, and explored 50+ cities as “digital nomads.” They started the Asian Wander Women community with the goal of bringing together like-minded women who aspire to do the same.Through tales of location independence, career ambitions while being on the move, dating and relationships, we unpack all of it and what it means to be an Asian Wander Woman. Tune in and be a part of the adventure! Explicit Tales Trails and Taverns Joseph Gelinas Here we will be exploring haunted woods, forests, taverns, bars and breweries. Any where I can visit that has a storied or haunted history, will be explored and discussed. As long as there's a personal story in a haunted location, and somewhere close by I can get a beer, it'll be on this podcast. Hiking Stories by "Tales Trails and Taverns" Written and Produced by Joseph Gelinas Spreadshirt Talestrailsandtaverns.com patreon.com/Talestrailsandtaverns Explicit Love Thy Neighbourhood Time Out London Time Out London editor Joe Mackertich invites famous Londoners to show him around their favourite bit of the city. Listen in as your favourite celebs share tall tales and weird anecdotes about the spots they love. One area, four locations: it’s time to learn to Love Thy Neighbourhood. A new episode every Tuesday. Find these places for yourself on our Love Thy Neighbourhood Apple Maps guide here & save to stay up to date. Explicit

Frequently Asked Questions

How long is this episode of Gypsy Tales?

This episode is 3 hours and 15 minutes long.

When was this Gypsy Tales episode published?

This episode was published on August 14, 2026.

Can I download this Gypsy Tales episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!