Watch Sailing & Boating Adventures Around the World
Explore sailing, boating, and water sports through our curated video archive. From epic sea voyages to serene diving escapes, discover unforgettable adventures from top YouTube creators. Start your journey. Dream big. Sail far.
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The $10,000 Sailboat Isn’t Dead You’re Just Doing it Wrong
Can you still buy a good sailboat for $10,000 in 2026? If you’re looking for cheap sailboats for sale, buying your first sailboat, or wondering how much it costs to own a sailboat, this video is for you. Affordable sailing is still possible, but buying a cheap used sailboat today takes a different a...
Introducing Frederick Sailing! Sailor James & Victoria’s New Sail Training Business!
James Frederick and Captain Victoria Paul announce the launch of Frederick Sailing, offering world-class maritime training from Southern California to the Caribbean.
There was a sailing club in our backyard, and we didn’t even know it!
In this video we might just be starting our best sailing adventure yet! We are leaving the Caribbean behind, and joining the Oklahoma State Sailing Club right in our own little community of Stillwater, Oklahoma. As it turns out anyone in the community can become a member, not just college students...
The Reality of BOAT OWNERSHIP May be Tougher than you think! – (Episode 370)
In this episode we give Matt and Naomi a crash course in sailing, on their new to them fountaine Pajot catamaran in the south of France. But they dont have ordinary jobs, they have a YouTube channel with 10 million subscribers doing something called ASMR Mukbang! you can check out their channel at @...
A Near-New Catamaran for €100K. I’d Still Walk Away. | Sailing Truth Show
📕 GET THE BOOK: Be The Captain. Winner of the 2026 Eric Hoffer Award. 25 years of offshore decisions in one book → 🔓 FREE: The Captain's Locker. Printable watch schedules, pre-departure checklists, delivery tools → She's a 2023 Lagoon 42, almost zero hours on the engines, loaded with wa...
DEAL or DISASTER: YachtWorld’s Wildest Listings | Sailing Truth Show
📕 GET THE BOOK: Be The Captain. Winner of the 2026 Eric Hoffer Award. 25 years of offshore decisions in one book → 🔓 FREE: The Captain's Locker. Printable watch schedules, pre-departure checklists, delivery tools → Every week the brokerage sites are full of boats wearing a price tag that has...
How to sail a Catamaran in 2 min
How to sail a catamaran.
Can I sail into the wind?
How to sail upwind. Explanation of sailing techniques, directions of sail, how sail works and aerodynamics of sailing.
BIG ANNOUNCEMENT + We Almost Bought a Dismasted Sailboat! EP 201
Big sailing announcement! In this episode, we share a long-overdue life update and explain why we almost bought a dismasted sailboat. It’s been a while, so we’re catching you up on everything we’ve been working on behind the scenes and what’s coming next for us and the channel. We talk through a r...
What Went Wrong — Lessons from S/V Escape
This video took me three years to make. Two sailors lost their lives aboard S/V Escape, and this is a careful, experience-based breakdown of what went wrong to understand the seamanship lessons that matter. Captain’s Locker — FREE DOWNLOAD Gear, checklists, watch schedules, night-reef cards, emerge...
I Fell Asleep and Crashed Into the Rocks
Get The Book → The True Story Behind the Night I Almost Lost Everything—and What It Taught Me About Command at Sea. Two boats. Two oceans. Two mistakes I’ll never forget. This is the night I fell asleep under full sail and ran my boat straight into the reef—twice. It’s not about drama; it’s about...
An update you’re not expecting!
Thats right! We're starting a private charter business with Sitka in the San Blas Islands!! Click the link here to check out our website and inquire about booking ➡️ Thank you to everyone who watches, supports and has contributed to our journey. We love and appreciate you all.
Sailing is Easy & Fun – How to learn sailing
Sailing is easy and fun. You can learn quickly. Simple, quick and practical demonstration of how to sail on a sailboat. Filmed in Austria, lake Ossiach. Boat type is Monas. SUBSCRIBE to my channel:
How not to Sail
How not to sail. Simple, quick and practical demonstration of how to sail and not sail on a sailboat. Filmed in Austria, lake Ossiach. Boat type is Monas. SUBSCRIBE to my channel:
How to Sail in 3min
How to sail in 3min. Simple, quick and practical demonstration of how to sail on a sailboat. Filmed in Austria, lake Ossiach. Boat type is Monas. More How to Sail videos: SUBSCRIBE to my channel:
Did We Love It or Hate It? (Our Honest Catamaran Verdict) | Ep. 11
This is the final chapter of our 11 part series in which we officially kick off the Serenity SV adventure. Did we love it or did we hate it? Stick around until the end to find out. In this episode, we leave Hope Town and head over to Marsh Harbour to drop off Carissa and Robert. Then we take more sa...
Near-Death At Sea: What I Learned
Chapter 13 of my book *Be The Captain* is Storm Tactics: This is what I learned the night our catamaran cracked open 100 miles offshore. It wasn’t a rogue wave. It wasn’t one bad call. It was a chain of decisions—some rushed, some careless, some just unlucky. And the truth is, the biggest problem...
What Happens If You Never Clean Your Boat Propeller?
Support on Patreon: After 6.5 months of not moving, my sailboat’s propeller was nearly useless—forcing me to dive in and clean it by breath-hold. In this video, I take you through the challenges of underwater maintenance, the unpredictable wind of Greece, and deeper thoughts on why most modern sail...
My Catamaran Split in Half 100 Miles Offshore. Here’s How We Survived.
Get my book here: I've shared pieces of this story before, but never the whole experience—until now. This is the true account of the night my catamaran literally ripped itself in half, 100 miles offshore in the Pacific Ocean, and how my girlfriend and I managed to survive against incredible o...
Sailing Banana Pancakes is live! Join us as we answer all your burning questions, & what’s next!
March 30, 2025 Q & A Live Join us LIVE as we answer all your burning questions about our next big adventure! We’re sharing our plans for finding a new boat—Leopard 46 or Leopard 50? Plus, when we plan to leave, where we’re headed next, and reflecting on our past episodes from Season 1. We’ll al...
How to Heave-To Offshore: Real-Life Demo on a Yacht Delivery
Join me aboard a Beneteau 47.7 as we tackle offshore conditions 400 nautical miles north of Cartagena, Colombia, during a yacht delivery from Exuma, Bahamas. In this video, I’ll show you step-by-step how to heave-to in the wind and waves, offering crucial techniques every offshore sailor should know...
Ryan’s Caribbean sailing lessons | SAILING SUNDAY Vlog. 251
Ryans Sailing lessons in the Caribbean! Join us this week as we take you all over the Bahamas visiting amazing places with Ryans parents, and lets now forget his lessons on sailing as he teaches boat safety, anchoring and how to bring out the sails for his parents lol..... LAST WEEK the Island of C...![No Bikini, No BS – Kate Shows You How To Sail Upwind In Patagonia [Ep. 126]](https://i.ytimg.com/vi_webp/9b1QsdoIrD0/mqdefault.webp)
No Bikini, No BS – Kate Shows You How To Sail Upwind In Patagonia [Ep. 126]
This is how to sail in Patagonia. 100% Real Adventure Sailing! Dive into the epic sailing footage you've been longing for as Kate reveals the ultimate guide to sailing upwind and conquering the breathtaking waters of Patagonia. #sailing #sailingpatagonia #howtosail Want to support our content...