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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Broken Rudders, Sunken Boats: The Orcas Are Winning | Sailing Truth Show
Orcas have been ramming rudders and sinking sailboats off Spain, Portugal, and Gibraltar — and tonight we roll the tape. This is a Captain's Breakdown: I pause the footage, judge the crew's decisions in real time, and give the verdict — seamanship, panic, or pure luck. Then I'll tell ...
The Best Canadian Sailboat You’ve Never Heard Of | 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 1996 Gozzard 44, built by one family in a small Ontario shop th...
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...
We Sailed to a FORBIDDEN ISLAND | Sailing Truth Show
Most boats never make it to Mai'O. You can't just sail in... the island decides who comes ashore. Years ago, my girlfriend and I were anchored in Moorea when we met a man whose friend was from Mai'O. He asked if we could bring his friend home. We said yes — and what happened next was...
The Trouble with Cored Hulls | Sailing Truth Show
CELEBRATION: "Be The Captain" is officially a finalist for the Foreword INDIES Book of the Year Awards! Buy "Be The Captain" and get 20% off any PredictWind membership! (Discount link sent via email after purchase): Today’s Topic: The Hallberg Rassy "T-Bone" Reality...
50+ KNOTS: Survival Tactics & The Danger of “Growlers” | Sailing Truth Show
You'd better tether in for this one! We're discussing what actually happens when the wind exceeds 50 knots offshore, and what real options you have when it does. At that point, you don’t have unlimited choices. You have a few. In this Sailing Truth Show, we break down: • Heaving-to vs....
Sailing Truth Show: Can production boats make good cruising boats?
Can production boats actually make good cruising boats? I recently stepped aboard a nearly new Hanse 588, and I’ll be honest—it was huge, beautiful, modern, and incredibly appealing. And it raised a question I hear all the time from sailors planning to cruise: Are production boats actually good cr...
How People ACTUALLY Make Money While Cruising (No BS)
Most people don’t give up on cruising because of weather, boats, or seamanship. They give up because they can’t figure out the money. In this episode, I break down how people actually make money while cruising—and just as importantly, what doesn’t work once real life at sea gets involved. This is...