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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25 People Abandoned an UNSINKABLE Boat. It Came Back Without Them | The Joyita
In October 1955, the Joyita, a 69-foot motor yacht chartered for a routine supply run, set sail from Samoa for the Tokelau Islands with 25 people aboard. She was an incredibly sturdy, oak and cedar ship packed with five inches of solid cork insulation—making her physically incapable of sinking. Whe...
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 ...
My Final Video as Sailing Zingaro
After 10 years and 90,000 nautical miles, this is the last video under the Sailing Zingaro name. In 2016 I bought a catamaran, pointed a camera at myself, and made a promise: I'll go, and I'll take you with me. The good, the bad, the ugly. You watched me sail to Ecuador, Easter Island, an...
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...
He Did Everything Right. His Captain Still Blamed Him.
👉 Shape this book and get the free first chapter: A guy learns to sail, earns his certifications, and signs on to crew a delivery to San Diego with two strangers who talked a big game about their offshore miles. On his watch the autopilot quits. The wind builds, the seas build, and when he calls f...
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...
This sailing technique saved my butt (Why does nobody teach this?)
1,800 miles from the nearest road, my autopilot exploded into pieces on my lap. Three and a half days into an 18-day crossing from Ecuador to Easter Island, on a light catamaran with small rudders and no displacement, the wheel pilot's ring snapped, the belt cut itself in four places, and the b...
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...
Ever Been Seasick? Here’s how to fight it… | Sailing Truth Show
Since you’re leaning into the "Sailing Truth Show" angle, the description needs to feel less like a "vlog" and more like a masterclass. You want to hook the casual viewer who is afraid of getting sick, while establishing yourself as the authority who has written the book on the s...
Robert Perry: The Greatest Cruising Boat Designer? | Sailing Truth Show
Is Robert Perry actually the greatest cruising boat designer of all time, or is the "Perry Legend" just clever marketing from the Taiwan boat era? Today, I am putting my 18 years of living aboard and 60,000 miles of Navy submarine navigation experience to the test to judge the "Sailin...
How to Buy (and Sell) a Sailboat | Sailing Truth Show
🏆 AWARD NEWS: Be The Captain is officially a finalist for the Eric Hoffer First Horizon and Foreword INDIES Awards! Grab your award-nominated copy here: Most people buy the wrong boat for the wrong reasons, and they get buried in the paperwork they didn’t see coming. In today’s "Sailing Truth...
Be The Captain — Chapter One: Think Like a Captain (Audiobook)
This is the introduction and first chapter of the Be The Captain audiobook, read by the author. Chapter 1 is called Think Like a Captain. It's not about sailing techniques or gear. It's about command, and the mindset that separates people who make good decisions offshore from people who d...
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...
Using AIS offshore (PredictWind Masterclass 4/5)
Up to this point, we’ve focused on planning and interpretation. But once you’re actually offshore, your job as Captain changes. It moves from "making a plan" to monitoring the outside world and catching problems before they start. In this fourth video of our 5-part series, we’re looking at...
How I Read the Weather After 85,000 Miles (PredictWind Masterclass #1/5)
The ocean doesn't care about your plans. But it does respond to physics. After 85,000 miles at sea and a career as a Navy Submariner, I’ve learned that PredictWind is only as good as the person making the decisions. This is the first video in a 5-part intensive series designed to transform you ...
How I Choose a Weather Window (Plus: Signing 4,000 Books!) | Sailing Truth Show
Buy "Be The Captain" and get 20% off ANY PredicWind membership: Most sailors open a weather app and wait for "perfect" conditions that never come—or worse, they leave in a dangerous window because they don't know how to read the data. Today, I’m taking you behind the scene...
I Didn’t Expect This… Sirius Might Be the Smartest Sailboat I’ve Toured
Last chance for the first printing of Be The Captain → I want to set expectations for this video, because this isn’t a review and it’s not a sales pitch. This was my first time ever stepping aboard a Sirius sailboat. I didn’t come in with a script, an agenda, or any affiliation with the builder. ...
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...
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...
Sailing Truth Show: Why Balance Beats Strength on a Sailboat
Most people think surviving storms offshore is about having a strong boat. Heavier. Tougher. Overbuilt. It’s not. Offshore seamanship is the art of keeping a boat in balance—aerodynamically, structurally, and mentally. When a boat is balanced, energy stays manageable. When it’s not, energy builds ...
Where to Find REAL Sailing Information
Sailing knowledge isn’t centralized — it’s tribal. You learn from old salts, obscure blogs, long-out-of-print manuals, and the people who’ve actually done the miles. But with so much noise online, where do you find information you can actually trust? In this video, I’ll share the best places to lea...
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...