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 Intro1:54 Welcome Charley Boorman to Gypsy Tales2:26 Jase on the Subscribe Discovery4:57 Meeting Charley at the Isle of Man TT10:16 The David Jeffries Story14:40 Cardo Systems Ad22:01 Riding Australia End to End25:49 Living in Queensland with Jason Connery's Mother34:57 Racing the Dakar Rally37:07 The Race to Dakar Documentary40:04 What It Takes to Make the Dakar50:54 Coming Back to Dakar52:13 Jumping Into Long Way Down54:37 The Real Story Behind Long Way Round1:03:47 Getting the Sky One Deal1:07:06 Motosport Ad1:13:54 Collecting Dream Motorcycles1:24:05 Why Ewan Wanted to Do the Trip1:30:04 Riding Into Russia1:38:38 Jase's Scottish Roots1:39:33 Through Mongolia1:41:12 The Road of Bones to Magadan1:45:51 Magadan to Anchorage1:51:05 Long Way Round1:58:19 How Long Way Round Inspired So Many2:04:27 Fist Handwear Ad2:07:51 The Making of Long Way Down2:12:58 Africa in All Its Vibrance2:19:04 The Dangers of Border Crossings2:32:29 Charley's Dream Australian Ride2:36:56 Ducati's Desert X2:37:38 The Bike Charley Bought Himself2:42:41 53 Miles of Hard Enduro at the Isle of Man with David Knight2:47:04 What Makes Elite Riders Different2:47:40 Sota Fuel Ad2:48:28 Why Jett Lawrence Is So Good2:51:43 How Soccer Players Handle Injuries vs MotoGP3:00:58 Charley's Bucket List Rides3:07:38 The European Bucket List Tour3:14:02 Closing 📸 FOLLOW GYPSY TALES ON INSTAGRAM: @gypsytalespodcast 🛒 Shop Gypsy Tales merch: https://gypsytales.com 💼 Business inquiries: [email protected] 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

NOW PLAYING

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.

No similar podcasts found.

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!