Watch Sailing & Boating Adventures Around the World – Page 4 of 43
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 73-96 of 1023 results
3 Fails in 3 Days… Puerto Rico Didn’t Go As Planned E377
Not every sailing day goes to plan… and this one REALLY didn’t 😅 We kick things off with a beautiful, calm sail past Cabo Rojo Lighthouse—one of the most stunning coastlines in Puerto Rico. But from there… things start to unravel. We anchor in La Parguera hoping to experience the famous biolumines...
Everyone Hates This Sailboat… So Why Do People Love It?
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Why Would Anyone Want a Trimaran?
Why would anyone choose a trimaran over a monohull? In this video, we compare the Dragonfly 36 trimaran vs a Beneteau Oceanis 40.1 to answer one of sailing’s biggest questions: are trimarans better than monohulls? We break down trimaran vs monohull pros and cons, including speed, stability, comfort,...
We Survived the MONA PASSAGE (47hrs Nonstop Sail to Puerto Rico) E376
After months of life in Luperón, Dominican Republic, it was finally time to move on… and take on one of the Caribbean’s most notorious crossings — the Mona Passage. We set sail for Puerto Rico on a 47-hour, 245 nautical mile passage, pushing through a double overnight sail with little sleep and sea...
Why Are Whales Sinking Sailboats?
Why are whales sinking sailboats? Over the last few years, reports of orcas attacking sailboats have exploded across the sailing world, particularly off the coasts of Spain, Portugal, and the Strait of Gibraltar. Sailors have reported killer whales targeting rudders, disabling steering, and in some ...
This Was Our Toughest Hike (Isabel de Torres) + Our Final Luperón Days
This one tested us 😅 We took on the steep and slippery climb up Isabel de Torres in Puerto Plata—and it was no joke. Muddy trails, sketchy footing, and a serious leg burn… but the view at the top made every step worth it. Sitting above the city with a mini botanical garden and that iconic statue, i...
Why Most People Quit Living on a Sailboat
Living on a sailboat sounds amazing… until reality sets in. In this video, we talk honestly about why most people quit living on a sailboat. Not the romantic Instagram version. The real, day-to-day challenges that catch people off guard and slowly wear them down. If you’re thinking about: • living o...
The Cheapest Modern Sailboats You Can Actually Live On
Can you live on a sailboat if you’re not a sailor? Yes. And it doesn’t have to be expensive, old, or uncomfortable. In this video, we’re talking about the cheapest modern sailboats you can actually live on. Not performance boats. Not ocean-crossing yachts. Just modern, affordable, floating homes tha...
Free Sailboat Living The Only Way It Actually Works
Can you really live on a sailboat for free? Not the Instagram fantasy version — the real, practical version. In this video, we break down how people actually live on sailboats for little to no monthly cost, using real systems that work in the real world. This isn’t about hacks or shortcuts. It’s ab...
A $5,000 Sailboat Can Cost You $40,000 – Ep 371 – Lady K Sailing
So you found a $5,000 sailboat. It floats. It has a mast. The owner says “just needs a little TLC.” What could possibly go wrong? In this episode of Lady K Sailing, we break down the real numbers behind “cheap” sailboats. Standing rigging replacement, new sails, chainplates, soft deck repairs, bu...
The Big Problem With Beneteau (It’s Not What You Think)
Are Beneteau sailboats really “bendy,” cheap, or unsafe — or is the internet just yelling again? If you’re a middle-aged couple thinking about selling the house, buying a sailboat, and cruising to the Bahamas or the Caribbean, chances are a Beneteau is already on your shortlist. They’re everywhere ...
Taswell: The Secret Bluewater Yacht Built Like an Oyster
Are Taswell yachts the best-kept secret in bluewater cruising? In this video, we take a deep dive into Taswell yachts and compare them directly to one of the most respected names in offshore sailing: Oyster Yachts. Using real-world listings, we show how a Taswell 56 can sell for hundreds of thousan...
No One Wants This ISLAND PACKET 44! Ep 367 – Lady K Sailing
The boat for sale: Why is a 44-foot bluewater cruising sailboat priced so low? In this video, we take a deep dive into a 1994 Island Packet 44 that looks suspiciously cheap for its size, reputation, and offshore capability. Island Packet sailboats are known for being strong, conservative, full-ke...
Goodbye Catalina The End of America’s Favorite Sailboat Brand
For decades, Catalina Yachts was the front door to sailing in North America. If you learned to sail, cruised your first coastline, or ever thought “maybe this could be my life,” there’s a good chance a Catalina was involved. But right now, Catalina isn’t building boats. Production has paused. The ...
WHICH WOULD YOU TAKE? Ep 366 – Lady K Sailing
If you woke up tomorrow and won a sailboat lottery, but the prize wasn’t cash… it was a choice between two very different 47-foot sailboats, what would you do? In this video, we dig into a question that accidentally went viral on Facebook: Island Packet 439 or Beneteau Oceanis 47? Same size. Very...
Why is this Catamaran So CHEAP? – Ep 365 – Lady K Sailing
Why is this catamaran so cheap? 🤔⛵ Today we’re taking a deep, honest look at a Fountaine Pajot Mahé 36 Evolution, a real cruising catamaran that can sometimes be found for a shockingly low price compared to newer multihulls. Fountaine Pajot is one of the most respected catamaran builders in the wor...
These 4 Designers Built the Best Sailboats Ever – Lady K Sailing – Ep 364
Most sailboats are not accidents. They are the result of a few brilliant minds who figured out how to turn wind into speed, safety, and beauty. In this video, we break down the four sailboat designers who shaped sailing as we know it — the men whose ideas still influence the boats we buy, sail, and...
Learning to Sail: 5 Things I Wish Someone Told Me on Day One – Lady K Sailing – Ep 363
Sailing for beginners is a minefield of mistakes. You're watching the wrong videos. Most sailing advice skips the painful, embarrassing realities of Day One. I’ve sailed for years, and these 5 crucial things would have saved me thousands of dollars and years of struggle. Docking is terrifying. ...
The Worst Catamaran Ever Made (The Wildcat 350 Controversy) – Ep 362 – Lady K Sailing
Thinking about buying a Wildcat 350? Or just curious why this catamaran sparks so much controversy? In this video, we dive deep into the infamous Wildcat 350, the South-African-built catamaran with a reputation that swings wildly between “underrated gem” and “floating science experiment.” I found o...
Safest OLD Sailboats – Ep 361 – Lady K Sailing
What are the safest old sailboats ever built? In today’s episode of Lady K Sailing, we break down five legendary, storm-tested, ocean-crossing classics that earned their reputations the hard way. These boats aren’t about luxury or modern styling — they’re about survival, stability, and real offshore...
Everyone Should Own a Sunfish (Here’s Why) – Ep 360 – Lady K Sailing
The Sunfish is the best-selling sailboat of all time — over half a million built — and for good reason. It’s simple, portable, affordable, nearly indestructible, and one of the purest ways to learn and love sailing. Today, I’m diving into why the Sunfish became a legend, why it’s still one of the mo...
This $59,900 Sailboat Is READY to Sail Away Today! – Ep 359 – Lady K Sailing
Today we’re taking a deep dive into one of the best budget bluewater sailboats on the market: a 1984 Tayana 37 listed for $59,900. Yes… a real, offshore-ready, world-capable cruiser for under $60K — and you could quite literally buy it today and sail the Caribbean this season. In this video, we’ll ...
Perfect $20,000 Sailboat (Catalina 30 Refit on a Budget) – Ep 358 – Lady K Sailing
Could you really live on a sailboat for just $20,000? In this episode, we’re building the perfect budget cruiser — the legendary Catalina 30 — and transforming it into a self-sufficient liveaboard for under twenty grand. We’re adding 800 watts of solar power, a 300 amp-hour lithium battery, fixing ...