Watch Sailing & Boating Adventures Around the World – Page 8 of 51
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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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....
This Shipwreck Is FOR SALE for $100,000!?
Be The Captain — A Practical Field Manual for Offshore Sailors Hardcover + instant audiobook: 👉 There’s a shipwreck sitting on the bottom… and someone is asking $100,000 for it. But what is a sunken boat actually worth? In this video, we break down the real economics behind a shipwreck for sale — ...
Route Planning My Solo Nonstop Circumnavigation
Westerlies, doldrums, Cape Horn, and the most volatile ocean on Earth. This is the route that will either work… or break me. And today I map the journey with a sailor who’s actually done it. 📺 Check out Jerome's YouTube channel here: @SailingIntoOblivion 🎙️ And his excellent podcast here: I...
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, ...
When back ups become the plan – offshore sailing to Scotland – Ep 264
Join us as we prepare to sail offshore in the North Atlantic in our custom aluminum sailboat from the nordic region of the Faroe Islands to Scotland, United Kingdom. We tackle failed Raymarin electronics, life on passage in the North Atlantic before dropping the hook in the beautiful outer hebrides!...
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...
EXPLORING $700 MILLION TUNNELS DEEP UNDER THE SEA – Ep 263
We continue our sailing journey in the Faroe Islands, exploring Tórshavn, the historic Tinganes grass-roofed buildings, and the dramatic landscapes that make this place feel unreal. From the marina, exploring by foot to driving deep under the ocean through the Eysturoy Tunnel and around the world�...
Sailing 3,000 Miles Across the Pacific on a 33ft Sailboat
“A ship in harbour is safe — but that’s not what ships are built for.” In May 2025, after months of preparation, we left Baja, Mexico, aboard our 33ft sailboat, setting out on our first true offshore passage that took us nearly 3,000 nautical miles to Hawaii. The early days tested us: light winds, ...
Giving Our Sailboat Some TLC | Deep Cleaning, Tweaks & Repairs! Ep-203
We finally turn south and commit to the big decision — crossing the Pacific 🌊 With a huge passage ahead of us, it’s time to stop procrastinating and start ticking off the long job list. In this video, we head into Hammock Beach Marina for a few nights to give Escapade some much-needed TLC. From dee...
Sailing Truth Show: The MOST Important Question Before You Buy a Boat
Thinking about buying a boat or going cruising? Read this first: Most people think buying the right boat is the hard part. It isn’t. The hardest part—and the part almost nobody slows down enough to think through—is whether this life actually fits who you are. In this Sailing Truth Show, we’re h...
Sailing in France: Golfe du Morbihan to Brest, Part 3 | DrakeParagon
It's important to keep your wits about you when sailing this close to the coast of France, especially at night! And while we'd like to think that everyone keeps a vigilant watch while underway, that is often not the case. So what happens when two boats are on a collision course at sea? *...
why these tricky seas are worth sailing – Ep 262
Join us as we cruise deep into the fjords of the Faroe Islands - part it the United Kingdom of Denmark. We sail into the island of Borðoy where we explore Klaksvik and its jaw dropping beauty. We go on adventures hiking, to the famous Klakkur summit , wild landscapes and mountain views overlooking t...
Sailing Truth Show: Real Offshore Sailing Questions – Answered
This live stream is built entirely from real questions pulled straight from the comments on recent videos. No slides. No scripts. No armchair theory. We’ll cover real offshore sailing topics—storm tactics, reefing, routing, boat design, fatigue, risk, and judgment—and talk about what actually work...
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. ...
Getting failed Raymarine electronics working again & 49kt winds: Cruising the Faroe Islands – Ep 261
After a tough sail from Iceland to the Faroe Islands with failed instruments and 36 hours straight of hand steering, we finally arrive and begin exploring the Faroe Islands by boat. This episode follows our time in Eiði, hiking above dramatic sea stacks, waiting out strong winds, repairing our elect...
Sailing Truth Show: When Is It Time to Give Up the Sails?
Interested in sailing offshore? Here's what you need to know: When is it time to give up the sails? This livestream is a reflective conversation about sailing, aging, fatigue, partnership, and changing priorities—not a sail vs power argument. We’ll start with an excerpt from Skip Novak, exp...
Choosing the Window | Leaving San Blas & Sailing to Shelter Bay
After weeks anchored in the San Blas islands, it was time to move again. In this episode, we leave the Swimming Pool anchorage and begin our passage toward Shelter Bay. The weather window wasn’t perfect — the seas were rolly — but with lighter winds and tougher conditions building ahead, it was the ...
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...
45 GRUELING HOURS OFFSHORE that almost broke us – Ep 260
In this episode, we depart Seyðisfjörður, Iceland in late September to begin an offshore sail to the Faroe Islands along a historic North Atlantic route. What started as a routine passage quickly turned into a demanding crossing that tested our endurance and seamanship. We share the realities of off...
STORM AT SEA: Through the Eyes of a Yacht Captain | Strait of Malacca
#sailingstorm, #yachtstorm, #stormatsea, #sailingadventure, #yachtcaptainPO Сan a sailing yacht survive a direct lightning strike in the middle of the ocean? In this video, experience a tropical storm through the eyes of a yacht captain — from a breathtaking sunset to the absolute chaos of a midnig...
LIVEABOARD ESSENTIALS: STUFF WE SWEAR BY ON OUR BOAT! EP-200
Go to and use code ESCAPADE to get 5% off your Holafly eSIM for your next trip! 🌴 Check out our favourite things for living aboard—practical, space-saving, and just plain useful! THE GALLEY 🍳 Collapsible Tupperware Set (Various Sizes): Small Collapsible Tupperware: Clip-On Strainer: Collapsi...
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 ...