Watch Sailing & Boating Adventures Around the World – Page 2 of 6
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 25-48 of 125 results
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 ...
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...
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.
What seems to be the problem? (Engine failure diagnostics) raw & extended | Sailing Sitka Ep 171
Jay and Kenna sail back to Linton Bay in order to get their engine in top notch after having experienced multiple failures. They spend countless hours over the course of a few days eliminating what could be the culprits while on anchor, but they won't know if they solved it until they put it to...
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...
Near-Death At Sea: What I Learned
Chapter 13 of my book *Be The Captain* is Storm Tactics: This is what I learned the night our catamaran cracked open 100 miles offshore. It wasn’t a rogue wave. It wasn’t one bad call. It was a chain of decisions—some rushed, some careless, some just unlucky. And the truth is, the biggest problem...
Light at the End of the Tunnel… Or Was It? | Sailing Sitka Ep 169
Jay and Kenna finally breathed a sigh of relief after securing a new propeller for their outboard—a mission that took a grueling 9-hour sail to complete. With that crucial task checked off, they took time to regroup in Linton Bay, refueling, stocking up, and tackling laundry and water runs. For a mo...
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...
Back Onboard! – Living With The Tide
Welcome aboard! After a couple of years away, we're back on YouTube with a new boat, a new camera – but the same silly crew. Our previous adventures followed the restoration of Morna, our beautiful 100-year-old gaff ketch. Sadly, after many experienced boat builders came to take a look, it bec...
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 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 ...
Installing Starlink & Diesel Heat on Our Sailboat + Carbon Fiber Vacuum Bagging (w/ Ducks!)
From Racer to Home: Installing Starlink, Diesel Heat & Vacuum Bagging Magic! Plus Meet the Ducks! Welcome back aboard SV Another Adventure, where we’re turning a retired racing trimaran into our dream cruising/liveaboard sailboat—and this episode’s got a little bit of everything! 📡 We kick thi...
Engine Nightmare, Breakages & Bad Luck Continues… Panama Canal Day 2 | Sailing Sitka Ep 160
Panama Canal Day 2: Engine nightmare & bad luck continues, Atlantic awaits... In this episode jay and Kenna (along with @SailingSVBully ) continue their unexpected adventure through the Panama Canal with their unreliable engine. Their troubles aren't done with just yet. The bad luck sticks ...
Panama Canal Nightmare: Engine Failure, No Sails, Will we make it through? | Sailing Sitka Ep 159
Engine Failure in the Panama Canal: Will we make it or get Fined? In the very exciting episode of Sailing Sitka, Jay and Kenna ( along with their pals @SailingSVBully ) embark on their most stressful journey yet. The Panama Canal is an emotional strain already but adding an unreliable and untrustwor...
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
Jay and Kenna share some real thoughts and info as they prepare to transit the Panama Canal from the pacific to the Atlantic. But not before they enjoy some time enjoying the city life in Casco Viejo. Thanks for watching and subscribe if you enjoy. Stay tuned for next episode as it will be the one w...
Our last sail on the Pacific Ocean | Sailing Sitka Ep 157
Jay and Kenna embark on a 3 day passage sailing from the tiny village of Bahia Honda to the concrete jungle of Panama City. This sail happens to be their last in the Pacific Ocean as they get ready to cross the Panama Canal into Atlantic waters. Thank you for watching and please subscribe if you enj...
Sailing to a remote, timeless village on Panama’s pacific coast | Sailing Sitka Ep 156
Jay and Kenna sail further into Panamanian waters only to discover a hidden gem of a village which was completely stuck in time. Join us on this special 3 year anniversary episode as we sail to Bahia Honda on Panama's pacific coast and learn to live slowly as we discovery the simplicity and bea...
Sailing to Panama | Sailing Sitka Ep 155
In this video of sailing sitka, jay and Kenna sail to their first port in Panama from Golfito, Costa Rica. They anchor in front of a desolate little island consisting of nothing but tall standing palm trees and white sandy beaches. Thanks for watching and subscribe if you do!
Getting tattooed on a classic sailboat in Costa Rica | Sailing Sitka Ep 154
Jay and Kenna have sailed their 41 foot sailboat from Canada to Costa Rica of the period of 2 years. Such an adventure does not come without obstacles including trial and errors. During their travels in Central America, they also met a fellow offshore sailor who happened to be a tattoo artist and on...
Journey to the most protected bay in Costa Rica | Sailing Sitka Ep 153
In this episode of Sailing Sitka, Jay and Kenna sail the squally and sloppy seas from Quepos to Golfito, down the pacific costa of Costa Rica. After having numerous encounters with rolley anchorages, we finally make landfall in a bay that is often mistaken for a lake, thats how protected it is. Some...
Cruising Costa Rica on a 41′ Sailboat | Sailing Sitka Ep 151
In this episode of Sailing Sitka, Kenna and Jay sail from Bahía Ballena to Quepos on the pacific coast of Costa Rica.
THIS is why we sail offshore. | Sailing Sitka Ep 150
In this episode of sailing sitka, we sailed to Bahía Ballena here on the pacific side of Costa Rica. After some squally and rough seas, we were more than grateful to be anchored in such a postcard worthy anchorage. It really puts it into perspective exactly why sailors sail offshore... to arrive and...