Watch Sailing & Boating Adventures Around the World – Page 4 of 52
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 1230 results
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 CAPTAIN’S LEAVING | SAILING THE CARIBBEAN
THE CAPTAIN'S LEAVING | SAILING THE CARIBBEAN This week we're sailing north through the Caribbean, leaving the Grenadines and St Lucia in our wake as we make a fast passage towards Martinique. This isn't the slow island hopping journey we planned. Instead, we're on a tight sched...
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...
BLUEST WATER IMAGINABLE – TOBAGO CAYS
WE SAILED HERE - TOBAGO CAYS After weeks of hard work in a Trinidad boatyard, we sailed north through the Grenadines to pick up Declan and Ivan in St Vincent, then back tracked to the breathtaking, impossibly blue Tobago Cays, a tiny archipelago in the Southern Grenadines famous for it's cryst...
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...
SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD
SHIPWRECKS, SABOTAGE, BOAT WORK & LIFE LESSONS IN TRINIDAD BOATYARD This week we're experiencing the reality of boatyard life in Trinidad while finishing our haul-out, repairing systems, and discovering the unexpected kindness that makes the sailing community so special. While working agai...
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...
IS THIS SABOTAGE? | TRINIDAD HAUL OUT MYSTERY
IS THIS SABOTAGE? | TRINIDAD HAUL OUT MYSTERY Sand in our sail drive oil wasn't something we expected to find during a routine haul out in Trinidad. So how did it get there... and could it be sabotage? This week we haul out in Chaguaramas, Trinidad, one of the most popular and cost effective ...
We Had Never Heard of Heysea… Until This 50’ Catamaran Shocked Us | Seaview 50 Tour
We toured the Heysea Seaview 50 Catamaran at the Miami International Boat Show (MIBS) — and honestly… we were shocked. Before this boat show, we had never stepped aboard a Heysea catamaran (and barely knew the brand). But the Seaview 50 completely changed that. From the spacious salon layout to the...
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...
GOODBYE – BIG CHANGES at sea
GOODBYE - BIG CHANGES at sea Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] Welcome back aboard. This week we&#...
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...
LIFE – Sailing Grenada
LIFE - Sailing Grenada Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] Welcome back to Grenada, where we are soa...
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 ...
WHY WE WENT SAILING – the answer may surprise you!
WHY WE WENT SAILING Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] This week's sailing vlog we're bac...
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...
FROM HOSPITAL TO HERO – A KIWI’S WILD WEEK IN AMERICA
FROM HOSPITAL TO HERO - A KIWI'S WILD WEEK IN AMERICA Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] This ...
We Hand Built Our Latest Yacht Upgrade!
This project has been a long time coming! In this episode, we finally finish and install the custom carbon fiber table for the roof of our sailing catamaran, starting from a bare foam core and ending with a professional level finish.... we hope! 😅 A full-blown composite build, we cut and shape the ...
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...
SUSPICIOUS ENCOUNTER with BOATS SAILING OFFSHORE VENEZUELA COAST
SUSPICIOUS ENCOUNTER with BOATS SAILING OFFSHORE VENEZUELA COAST Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] ...
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...
WE DISCOVER ABANDONED OFFSHORE PRISON – SAILING FRENCH GUIANA
WE DISCOVER ABANDONED OFFSHORE PRISON - SAILING FRENCH GUIANA Thank you for helping keep us afloat and supporting the creative process. You can be part of the crew for less than the price of a coffee. You can do so here: - Patreon - Paymate - PayPal using our email [email protected] I...