Watch Sailing & Boating Adventures Around the World – Page 5 of 32
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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After the Fun in Sint Maarten, We Set Sail for Saint Kitts
After an unforgettable time in Sint Maarten—celebrating Bastille Day, ziplining through the lush hills of Loterie Farm, and soaking up the cruiser-friendly vibes of the lagoon—it’s finally time to hoist the sails again. In this episode, we say goodbye to the comforts and conveniences of Simpson Bay...
FAST. Rugged. World Ready! 2018 Marples 40 Trimaran. FULL TOUR!
#SailboatTour #Trimaran #Multihull #BluewaterSailing #BoatFools #boatfoolssailing #FastCruiser FAST. Rugged. World Ready! 2018 Marples 40 Trimaran. FULL TOUR! ASKING PRICE: $125,000 TOC: 00:00 Canadian Ken in down below 00:08 Intro - Fly over of the Marples Custom 40 CC Fast Cruiser 00:26 Up On D...
Boat Life in Sint Maarten: Dinghies, Beaches & Island Vibes
Yes, we’re still in Sint Maarten… and honestly, we’re not mad about it! We’ve been anchored in Simpson Bay for over a week now, and this island is quickly winning us over. Sint Maarten is truly a cruiser’s paradise—getting around by dinghy is easy and efficient, with everything you need just a short...
Would You Live Like This? The Reality of Island Life | Sailing Sitka Ep 174
Jay and Kenna have spent the past three years sailing from the Pacific Northwest of Canada to the remote San Blas Islands — cruising, connecting with local communities, and learning along the way. Now, life in this isolated island chain means days filled with games, beaches, cold drinks, and plenty ...
Package Delays & Island Days | USVI Boat Life
After our 7-day passage to the USVI, we find ourselves in island time — waiting on delayed packages before we can continue our journey south to Saint Martin for hurricane season. While we wait, it’s a week of boat projects and island adventures! We spend time troubleshooting a radar that won’t acti...
Off-Grid Sailing the Bahamas – Spearfishing, Boat Life & Beach Bonfires Ep-180
📲 Get an exclusive 15% discount on Saily data plans! Use code ESCAPADE at checkout. Download Saily app or go to We sail to the wild and remote Ragged Islands of the Bahamas—where boat life gets seriously off-grid. This episode is all about untouched sailing, spearfishing for our dinner, exploring...
We Finally Made It! 1,051 Nautical Miles to Saint Thomas 🌊⛵
After 7 days and 2 hours at sea, we finally made landfall in Saint Thomas! This was our longest passage yet — and our first without extra hands on deck — so we’re incredibly proud to have safely navigated 1,051 nautical miles as a family. Along the way, we battled rough seas and squalls, replaced a ...
Sailing back to Paradise | Sailing Sitka Ep 172
Despite recent engine troubles, Jay and Kenna felt the pull to keep moving. With their sights set on the tropical paradise of San Blas, they set sail from Linton Bay—upwind and into the chop. Will they make it? Hit subscribe to follow the journey.
Hurricane Season is Here! Sailing South to Trinidad
The first time we arrived in Trinidad we thought it would be for 3 months... 21 months and more warranty repairs and mistakes than we ever could have imagined, our Leopard 45 relaunched. Now, it's time to go back! Starting in the live aboard cruisers hub of Le Marin and Sainte Anne in Martiniq...
Our First Sail on our NEW Vision 444 Catamaran – Finally!
After weeks of stress and setbacks at Harbour Towne Marina, the moment we've been waiting for is finally here—we're pulling the dock lines and setting sail for the very first time aboard our brand new 2023 Vision 444 catamaran! Our destination: Xquisite Marina in Freeport, where the rest ...
Engine Failure… NOT AGAIN?! Feeling Hopeless in Rough Seas…| Sailing Sitka Ep 170
Jay and Kenna felt ready—prepared and excited to return to paradise. After a week anchored in Linton Bay, they set sail for what should have been a smooth trip back to the San Blas Islands. But that’s not how things played out.Pounding into relentless 10–14 ft seas on a lee shore, their engine faile...
Finally Sailing Again! Night Passage from St Martin to Guadeloupe
As the Caribbean hurricane season approaches it's time to start heading south! The episode begins with a surprise storm slamming the St Martin anchorage; high winds, rough seas, dragging boats - not good for someone who went out the night before! 😳 It's a quick insight into how unexpecte...
Better off Naked?! Rash ending to final days of Boat Life in Paradise – Ep 236
Get an exclusive 15% discount on Saily data plans! Use code JIBSEA at checkout. Download Saily app or go to Sailing the British Virgin Islands as our last stop in the Caribbean before we set sail for the high latitudes for our next big adventure on our new to us custom aluminum sailboat. In this ...
Small Catamaran or Big Monohull…BUYING a USED Boat and We Have NO Clue What We WANT – Ep. 272
We are looking to buy another boat and we have no clue what to buy! Buying a boat whether it´s new or used can be an overwhelming process. And even after 6 years of sailing around the world on our 2010 Beneteau Oceanis 43...we still have no idea what we want. Go for a big monohull or a small catam...
SAILING to One of the WORLD’S BEST BEACHES 🌴 EP-173
Sailing the Spanish Virgin Islands to Puerto Rico, we fly our colourful gennaker, explore world-famous Playa Flamenco, and anchor at stunning Palomino Island. Subscribe for more sailing adventures, boat life tips, and off-the-beaten-path Caribbean gems! #Sailing #PuertoRico #BoatLife Sailing the ...
NO SECRETS, NO FILTER: Answering all your questions during a DAY IN THE LIFE! – Ep 232
Thank you to everyone who sent in their questions. This was so much fun :) Join us for a full day in the life as full-time world travellers, sailors, and liveaboard cruisers! We're answering your biggest questions about what it’s really like to live off the grid, travel the world by sailboat, ...
St Lucia Adventure: Exploring the Majestic Pitons! Episode 45
Sailing St. Lucia After the Storm | Anniversary, Chocolate & Mud Baths! | Ep. 45| Banana Pancakes We’re back with another unforgettable episode of our sailing adventure—and this one’s packed with tropical storms, wedding anniversaries, chocolate EVERYTHING, volcanic mud baths, and a wild ride t...
CUTTING IT ALL DOWN! Transforming our Custom Built Aluminum Sailboat – Ep 230
Join us as we set sail from Ile Fourchue (an island of St. Barth's) to Sint Maarten/St. Martin for a major DIY welding project on our custom aluminum sailboat. We’ll be showing you how we’re preparing our boat for offshore adventures by completing crucial modifications, including TIG welding a...
We Know We’re Sailing Fast When Our Dog’s Ears Are Flapping Like Crazy – Ep. 271
In today’s episode, we’re taking the boat out for an epic sail from our slip in the Bahamas (lucky us, right?) to Guana Cay! We’re excited to check out what all the fuss is about at Grabbers and Nippers on a Sunday Funday. It’s a day full of sailing, cruising with friends, and even docking the boat!...
CHASING BUBBLES around the Virgin Islands! ⛵️ Let’s Bring Her Back WITH A BANG! 🎉 l ep.61
Get your free LMNT Sample Pack with any purchase at Also try the new LMNT Sparkling — a bold, 16-ounce can of sparkling electrolyte water. Join the Next Chasing Bubbles Regatta HERE (APRIL 9th, 2025)- You can charter a boat or sail in a vessel of your own...For more information and to keep up wit...
Let’s Get This Boat on a Lean: Epic Sailing Through the Bahamas! – Ep. 270
We’ve finally arrived in the Bahamas, and it’s as incredible as we remembered! The blue water is calling, and we couldn’t be more excited to explore. We find some secluded anchorages and untouched beaches, enjoying perfect sailing conditions with plenty of wind and smooth seas—just what we need to g...
Survey Day – Will BIG LOST Pass the TEST?
Today's the big day! The buyers have arrived at Ixquisite Catamaran Center in Freeport Bahamas to witness the full survey of Big Lost-the catamaran they plan to buy if all goes well. We head over to Bradford Marina, where Big Lost gets hauled out on the travel lift for a thorough hull inspectio...
Exploring the Island of Dominica: Hikes, Waterfalls, River Boat tour. Episode 42
Exploring Dominica: Waterfalls, Jungle Hikes & Our Last Adventure! 🌿💦⛰️ Join us for our last day in the lush jungle of Dominica! We started our morning packing up our VRBO and heading out for an adventure. First stop: Emerald Pool—a stunning waterfall with crystal-clear water. While Steve and t...