Watch Sailing & Boating Adventures Around the World – Page 2 of 3
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.
Showing 25-48 of 57 results
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...
This 12-Minute Video Will Save You $50,000 on a Sailboat
I charge $500 for a 90-min boat consultation. Today, for free, I'm giving you the forensic audit process I’ve developed over 24 years on the water, from nuclear submarines to offshore sailboats. Why this matters: * The Forensic Audit: How to list every system and calculate its true remaining ...
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...
30 Seconds. That’s What a Lithium Fire Gives You.
On June 10th, 2024, SV Theros left Halifax bound for the Azores. Three days later, their AIS signal went dark 34 miles southwest of Sable Island. Four weeks after that, Parks Canada found the crew on the beach. They had washed ashore in their inflatable dinghy. The Transportation Safety Board conclu...
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 Night I Almost Lost the Keel (and Why I Quit Deliveries)
In 2014, I delivered a Beneteau First 47.7 from the Bahamas to Cartagena. Somewhere in the Caribbean, 150 miles offshore, I found myself ankle-deep in water, crew vacuuming the bilge in the dark, batteries dead, no GPS, no autopilot. I didn't know at the time how close we were to losing the kee...
Mastering the Offshore App (PredictWind Masterclass 5/5)
[SPECIAL OFFER] Get 20% off PredictWind when you purchase Be The Captain! 📘 Grab your copy and unlock the discount here: 👉 Up to this point, we’ve focused on planning, interpretation, and strategic awareness. But once you’re actually offshore, the goal is clarity over features. In this fifth and f...
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 ...
Nigel Calder: The Truth About Philosophy, Gunboats, and Marine Engineering
Nigel Calder has kept more sailors safe than perhaps anyone alive. But his path to becoming the world's foremost marine engineering expert was anything but standard. Get my book Be The Captain: Support the journey on Patreon: In this interview, we dive into the stories you won't find i...
Why I’ll Never Trust a “Performance” Boat Again | Sailing Truth Show
I was in the middle of a delivery on a Farr 47.7, when the bilge pump went off... What followed was an insane story that nearly killed me. I'll NEVER take another 'performance' production boat offshore. In this episode of the Sailing Truth Show, I’m sharing the full, documented sto...
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....
I Didn’t Want to Love This Boat
📘 If you want to understand what actually makes a great offshore boat, Chapter 2 of my book breaks it down clearly and honestly: 👉 If you want to understand what modern offshore sailboat design looks like when it’s done right, this is a boat worth paying attention to. The Pegasus 50 isn’t flashy....
They Built This Boat Too Well
Learn what makes a great offshore boat, Chapter 2 of my book breaks this down in detail: 📘 Be The Captain — A Field Manual for Offshore Sailing This boat didn’t disappear because it was flawed. It disappeared because it was built too well. Boats like this were designed around seamanship, margin, ...
Your First Sailboat: No BS Advice for New Sailors
Stop trying to buy a "circumnavigation boat." Buy an "education" boat. I recently received an email from Simon, an 18-year-old sailor with a tight budget and a big dream. He said something that most beginners miss: "Ugly is fine. Stuck in a boatyard is not." Buying yo...
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...