Watch Sailing & Boating Adventures Around the World – Page 3 of 11
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 49-72 of 264 results
SAILING TO CANADA IN A ROCKET SHIP! (Finally in home waters!) – Ep 242
Sailing to Nova Scotia by sailboat during a 3-day offshore passage from Nantucket to Canada, we pick up on Day 2 sailing wing-on-wing across the North Atlantic. Join us as we cross open water, navigate changing conditions, and make a last-minute change to our landfall destination along the Canadian ...
SELLING OUR BOAT & HEADING INTO THE FOG – Ep 240
Join us on this epic offshore passage as we set sail from Virginia and head north to the stunning shores of Martha's Vineyard. From offshore champagne sailing conditions to the thrill of flying our spinnaker and Code Zero, to encounters with dense fog as we approach New England, it's a fa...
We Finally Made It! 1,051 Nautical Miles to Saint Thomas 🌊⛵
Connor and the crew aboard Sailing Big Lost complete a 1,051 nautical mile passage from Eleuthera to Saint Thomas, tackling engine repairs and squalls over 7 days at sea.
The Route Less Traveled: Our Passage South
Kelly and Connor navigate their Vision 444 catamaran through Current Cut and Eleuthera, troubleshooting rigging and fueling up for an open-ocean passage south into the Atlantic toward the Virgin Islands.
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...
AN UNEXPECTED DETOUR – WHEN SAILING PLANS MEET REAL LIFE
AN UNEXPECTED DETOUR - WHEN SAILING PLANS MEET REAL LIFE We finally sail into Cape Town after crossing the Indian Ocean and rounding the legendary Cape of Good Hope - one of the most iconic sailing passages in the world. But just as we reach safe harbour in Hout Bay, life throws us a surprise: Rob...
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...
“50 years of history GONE in a second…” | Sailing Sitka Ep 162
Jay and Kenna are in Shelter Bay Marina, fixing some minor and major problems they've encountered while transiting the Panama Canal, on top of that they do some routine and periodic maintenance to make sure their 50 year old sailboat is ready to sail her way toward the desolate and world-renown...
Sailing Big Lost: Our Story & Goodbye
At the Xquisite Catamaran Center in Freeport, Connor and Kelly Malone close escrow on Big Lost, their 2002 Leopard 62, detailing lessons learned from 4,000 nautical miles of cruising before downsizing to a smaller catamaran.
It’s OVER! Getting the BIG Anchor ⚓
That’s it. We Are Done! After 27 days and 3,718 nautical miles, we’ve officially crossed the Atlantic Ocean. What an adventure this has been! This journey has given us so much—more than just miles under our keel. We’ve gained knowledge, not only about sailing but also about the incredible places ...
Why our engine FAILED while transiting the Panama Canal | Sailing Sitka Ep 161
Jay and Kenna are now tied along a dock in Shelter Bay marina after undergoing two of the most stressful days of their lives. While transiting the Panama Canal, their Yammer 56 engine failed several times in the worst possible scenarios. Surprised they even made it all the way through, they now can ...
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 ...
Entering the DANGER ZONE
We are sailing through one of the most dangerous areas in the Atlantic Ocean. Orcas have been terrorizing sail boats near the Strait of Gibraltar since 2020. Nearly 700 incidents and at least 5 boats sank. This has played heavily on all our brains since we embarked on this adventure. No one knows wh...
Sailing 500 miles to the CANARY ISLES on a small boat
Jump on board with us with extra content AND ad-free videos ~ Support our Production▸ After a long descent of western Europe, we are now well placed to push off in to the Atlantic Ocean and head for the first stepping stone on this route. There is a good forecast of trade-winds and we get to proper...
The Au Natural Experience
São Miguel is famous for it volcanic landscape. It is a geothermal wonder! We relaxed in natural hot springs, soak in oceanfront pools, explored steaming volcanoes, and colorful crater lakes. It's nature’s spa in the Atlantic! We Have reached the halfway ⛵ mark on our Atlantic Crossing 🫣 *...
Diving into the Culture of the Azores
We have been couped up on this ocean for 14 days now and it’s time to blow off some steam. But maybe we went a bit overboard by jumping into a local cultural event of running with the bulls. 😲🐂 To be honest we didn’t even know the Azores existed until we began this journey. They are a group of 9 is...
NO FUEL & NO WIND a Nasty Combination
What do when you are 20 miles from land and the wind dies out and so does your fuel. Being adrift in the Atlantic Ocean is nothing less than terrifying. Now it's just a waiting game to see what happens next. ⛵ Almost to the Azores *If you missed any get caught up here* *LIKE, SUBSCRIBE &...
The Crew has gone INSANE ~ 13 Days at SEA
The mind does funny things to you when you have not seen land in almost 2 weeks. Crazy ideas start popping into your head and you start seeing things in a whole new perspective. But was this really the best idea? We Have reached the halfway ⛵ mark on our Atlantic Crossing 🫣 *If you missed any ...
Contessa 32 AND Rival 32 Sailing Offshore in Heavy Seas
Jump on board with us with extra content AND ad-free videos ~ Support our Production▸ We have just sailed down from Norway to western Europe, on our wee ship. In this episode - big autumn winds arrive on the Portuguese coast, and we spend a long night on anchor watch with 40 knots of breeze. We get...
Exploring Paradise: Shroud Cay Waterways, Warderick Wells & New Friends!
Sailing Big Lost navigates the mangrove creeks of Shroud Cay to swim the Washing Machine before sailing at 8 knots to Warderick Wells and hiking Boo Boo Hill.
Finally Getting a Taste of It : Day 7 Atlantic Crossing
Halfway across the Atlantic, the wind has finally arrived, sending us surging forward with whitecaps breaking over the deck. The boat heels hard, the rigging hums, and every movement demands balance. After days of slow progress, the energy is exhilarating—but weariness lingers. Salt crusts our ski...
First Time in the Exumas! Sailing Through Paradise 🇧🇸✨
Awaiting a weather window in Rock Sound, Eleuthera, the family aboard Big Lost mends a torn head sail with help from SV Atlas before crossing open water to Allan Cay in the Exumas to observe native Bahamian rock iguanas.
The Calm Before the Storm: No End in Sight
To be honest, this isn’t what we imagined when we planned for this trip. We’d braced ourselves for chaos—crashing waves, howling winds, and the raw power of the ocean. Now we must worry that we will not have enough fuel to make it across. If the wind doesn’t fill in soon, we may be stranded… *...