Watch Sailing & Boating Adventures Around the World
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 1-24 of 92 results
WE’RE BACK AT SEA! 🌴 San Blas, Boat Repairs & Insurance Update! Ep-235
Sailing the San Blas Islands, Panama after months of sailboat repairs, boatyard damage and an ongoing insurance claim! ⛵️🌴 After months stuck in the boatyard, Escapade is finally back on the water and we’re sailing again! In this episode, we take you along for our first week back aboard Escapade as...
SAN BLAS Panama — The Reefs That Sink Boats Here | SSL779
The San Blas Islands are one of the most beautiful places we have ever sailed. They are also one of the most technically demanding. Over 100 kilometres of coral reef protects this archipelago — and that same reef has ended a lot of sailing dreams. After 28 hours of open Caribbean, we arrived in Gun...
🌴 The Last Paradise Before the Pacific Crossing | San Blas Islands! Ep-227
After weeks of offshore passages, unexpected challenges, and nonstop movement, we finally wake up in one of the most beautiful cruising destinations in the world: the San Blas Islands of Panama. With only one day to explore before continuing our journey, we move Escapade into crystal-clear shallow ...
Sailing to the Caribbean’s Most Remote Islands! Ep-226
After a whirlwind week in Cartagena, it's time to continue our journey west. Before leaving Colombia, we make the most of our time ashore celebrating our friends' wedding and exploring one of the Caribbean's most vibrant cities. From island beach clubs and sunset catamaran cruises to...
We Finally Made it the San Blas “Swimming Pool”
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. In this episode aboard Sailing Big Lost, we finally trade the noseeums of Snug Harbor for sunshine, clear water, and one of the most iconic...
Rained Out in San Blas
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. We’ve had rain off and on since arriving in Panama, and as we begin exploring the San Blas—now learning their true name, the Guna Yala Isla...
Sailing Into Guna Yala: From Puerto Obaldía to Isla Pinos
We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tuesday at 10:30 AM ET. We’re a family sailing full-time, exploring the Caribbean and Central America aboard our sailing catamaran Big Lost. New episodes every Tue...
An update you’re not expecting!
Thats right! We're starting a private charter business with Sitka in the San Blas Islands!! Click the link here to check out our website and inquire about booking ➡️ Thank you to everyone who watches, supports and has contributed to our journey. We love and appreciate you all.
Our last sail | Sailing Sitka Ep 182
After two unforgettable months in paradise, Jay and Kenna lift anchor and set sail on a short 9-hour passage from Chicheme to Linton on Panama’s mainland. Along the way, they take in every last moment of beauty that this sailing lifestyle has to offer. Back in Linton, the focus shifts to preparing S...
The End of an Incredible Chapter | Sailing Sitka Ep 181
And just like that, Kenna and Jay reach their final stop in the San Blas, savoring every last drop of paradise. Between lazy island days and exploring a beachside shipwreck on a neighboring isle, they make the most of their tropical farewell. With the season’s end in sight, they ready the boat for o...
From Dreamy Anchorage to Pirate Drama | Sailing Sitka Ep 180
Jay and Kenna were about a week into a postcard-worthy anchorage—spending their days lounging on the beach, sipping cocktails, surrounded by friends and fellow sailors, soaking up the beauty of the sailing lifestyle. But with all that beauty comes a bit of chaos. The truth is, common sense isn’t so ...
Sailing Into Trouble: The Day Our Anchorage Was a Crime Scene | Sailing Sitka Ep 179
Jay and Kenna lift the hook and set sail from Green Island toward the stunning Holadaze Cayes, one of the most picture-perfect anchorages in all of the San Blas Islands. But just when we thought we’d found paradise, we suddenly found ourselves—and Sitka—in the middle of an active criminal investigat...
What it takes to keep this dream alive | Sailing Sitka Ep 177
Jay and Kenna have arrived at a new destination—Green Island, a stunning atoll tucked within the San Blas Islands. While this lifestyle often feels like a dream and looks like something straight off a postcard, it takes real balance to maintain it. Could you keep up? Subscribe, watch the journey, an...
Our boat nearly quit, but we didn’t! | Sailing Sitka Ep 176
Jay and Kenna set sail from the sheltered anchorage of Chicheme, continuing their journey through the San Blas Islands to a remote and desolate new spot—though, unsurprisingly, not without a few hiccups along the way.
3 Years Offshore Cruising: Here’s What We Really Think (raw update) | Sailing Sitka Ep 175
Jay and Kenna are currently anchored in the beautiful San Blas Islands, soaking in the cruising lifestyle — though, as always, the highs come with their fair share of lows. After weeks of battling persistent engine troubles, this week they think they've finally tracked down the culprit. It’s be...
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 ...
Slammed into at anchor in High Winds “It could’ve been so much worse…” | Sailing Sitka Ep 173
Anchored in the San Blas Islands, Jay and Kenna are still deep in engine repairs, chasing down a stubborn mystery air leak in their Racor fuel filters. Amidst the stress, a 50-foot charter boat loses its anchor hold and slams into Sitka’s bow—leaving behind damage. The ocean may be everyone’s playgr...
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.
The Man who built a 75ft Wooden Catamaran and Sailed the World | Sailing Sitka Ep 168
Jay and Kenna along with their pal Derek @ontongjava5441 the man who built a 75ft wooden catamaran on a beach with his own bare hands! He shared with us some stories, details on his boat, lessons learnt and favourite place in the world! Apart from that memorable encounter, Jay and Kenna sailed to L...
Getting delivered boat parts to the edge of civilization (FAIL) | Sailing Sitka Ep 167
While cruising through the San Blas Islands, Jay and Kenna unfortunately broke the propeller on their outboard motor. Given the remote nature of the islands, where services like Amazon Prime are unavailable, obtaining replacement parts can be challenging. However, there are local services that deliv...
Sometimes cruising doesn’t always go according to plan… | Sailing Sitka Ep 166
Jay and Kenna navigate the harsh realities of cruising. There are both challenges and benefits to sailing and both can rock your world. From fixing broken systems, to installing new ones and reaching for the medical kits with no healthcare facilities in sight, this is all cruising. Thanks for riding...
Sailing Off-Grid in One of the World’s Last Untouched Paradises | Sailing Sitka Ep 164
In this episode, Jay and Kenna welcome aboard their friends from Canada and give them the full tropical, sailing experience by island hopping and cruising through the San Blas islands. We are sailing off-grid between sand spit islands in search for adventure, wind and good times. Check it out and su...
San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
Jay and Kenna depart from Shelter Bay marina after a week straight of boat work and diagnosing problems. Finally, after stopping in Linton bay for one night, they sail to the desolate and world renowned San Blas islands. A dream come true. They've worked hard for years and the hustle has now tu...