Watch Sailing & Boating Adventures Around the World – Page 9 of 30
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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One Week In… Total Rudder Failure on Our 40ft Sailboat
One week into working on our sailboat and we’ve already hit a major setback… our rudder has completely failed and ceased. What started as routine maintenance to drop the rudder and inspect quickly turned into a disaster when we discovered the rudder fused into the bearing and housing that means a fu...
Sailing The Bahamas – Threading the Needle Through Shallow Coral Reefs! Ep-186
We set sail on an overnight passage from the Exumas to the Abacos, navigating shallow Bahamian waters and dodging coral heads along the way. Our goal? Reach the narrow channel between the islands before sunset. After arriving, we're greeted by a few forecasted storms in the Abacos—just as we’re...
Sailing Into a Storm | Greek Island Adventure to Skyros
🌊 Support the Journey: We set sail from a quiet bay on the island of Proso, heading toward Skyros — a place of tiny horses, lobsters, and ancient legend. What began as a calm journey quickly turned into a tense wait-out as a lightning-laden storm rolled in. On a sailboat, thunderstorms aren’t just...
The BIG SPLASH – Months of Work Pay Off! | Episode 309
Welcome back to WE|Sail! After 6 weeks of non-stop solo work on the hard, it's finally time for the moment we've all been waiting for - SPLASH DAY! While Erica recovers from achilles surgery back home, Warren has been grinding through an epic list of boat projects to get Va ready for th...
ONE STEP CLOSER! Pre-Splash Day Push with the New Crew | Episode 308
Welcome back to WE|Sail! The crew is here and we're SO close! 🛥️ Our amazing new crew just arrived to help us finish the final boat jobs before splash day. Warren's got his list ready and honestly, he can't wait to get back on the water and start sailing to Fiji! There's somet...
Swimming with Sharks, Pigs & Pink Iguanas?! | Exumas Adventure! Ep-185
Come island-hopping with us through the wild side of the Exumas! 🏝️ In this episode, we snorkel with nurse sharks, visit a lesser-known spot to see the famous swimming pigs, and meet the rare pink iguanas of the Bahamas. It’s one unforgettable episode exploring the Exumas' most iconic (and unu...
Everyone Talks About This Sandbar…
We’re anchored in Kāneʻohe Bay, Oʻahu, and after a rough start—including running aground on a reef (watch that episode here: finally make it to the iconic sandbar, where turquoise water, sea turtles, coral, and even a possible puffer fish await. Later, we hike up Chinaman’s Hat (Mokoliʻi) and wrap ...
First Look at Our New 40ft Sailboat! Full Boat Tour & Walkaround
Here she is! – we bought a sailboat! Meet Flying Freedom ⛵️, our new floating home and the start of our biggest adventure yet. In this video, we’ll give you a full first look and tour of our 40ft Freedom 40/40 sailboat, showing you around every corner before we start the work to get her ready for li...
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...
Nippers: The Beach Bar with a Naughty Reputation (We Had to Investigate) VLOG 292
This week’s episode is a fun one — we officially move into our new rental here in the Bahamas, take a day trip to the (in)famous Nippers Beach Bar with friends, and head out for a relaxed sail with the crew from SV Escapade. No big drama, just a little slice of what life’s looking like right now — ...
Sailboat Projects: FINALLY the Help Warren Needed! | Episode 307
Welcome back to WE|Sail! The finish line is finally in sight! After what feels like endless boat projects, we're so close to getting Va back out on the open water where she truly belongs. But just when we thought we'd have to tackle the final stretch alone, something incredible happened.....
Dropping Anchor in a Lightening Storm⚡️ | Sailing Sunday VLOG 291
This week’s video is a raw, unfiltered look at what sailing really looks like when a storm rolls in out of nowhere — and you’re trying to make it to safe harbour with a baby onboard. It's the kind of moment that reminds us why preparation matters… and also why sailing with a baby adds a whole ...
WE are in Two VERY Different Places! | Episode 306
Welcome back to WE|Sail... This sail free week we again dive into boat projects, with the fiberglass barbecue and cooler once again taking the lion share of attention. Also we check in with Erica and her surgery from tearing her achilles tendon. WE are starting to feel the pressure and struggle wi...
Boat Yard Hustle! Inside Our DIY Haul Out Projects
With our catamaran safe and secure on the hardstand there's boat work happening every day! This episode we're replacing a critical part of the anchor windlass, upgrading the interior with DIY boat curtains, and getting some things done on our tender, an unusual dinghy which is designed to ...
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...
SPORTY SAIL to Newfoundland with MASSIVE ENDING – Ep 244
Join us on this epic offshore sailing journey as we leave the calm beauty of Bras d'Or Lake, Cape Breton Island, and sail straight across the powerful Cabot Strait to St. John’s, Newfoundland! In this episode, we sail in big offshore waves, witness humpback whales breaching and approach the b...
NEW EPISODE – Tired of Boat Work ! Too Much to DO! | Episode 305
Welcome back to WE|Sail... Welcome back crew, this weeks video finds VA still out of the water and the work seems endless, we still have the electrical rework with the new battery bank, as well as finishing the fiberglass forms and the beginning of the actual fiberglass work. So much work still n...
FOR SALE: 2008 Beneteau Oceanis 46 – Ready to Sail
🚨 SV SUNDAY IS FOR SALE! 🚨 We're officially listing our Beneteau Oceanis 46 Owners Version for sale, a highly sought-after, bluewater-ready cruising yacht that’s been our full-time home and taken us safely all over Europe and the Caribbean, currently in the Bahamas. This 2008 model, affection...
Sailing Nova Scotia’s Wild Coast & Through the Middle of an Island – Ep 243
Join us as we sail the stunning coast of Nova Scotia, exploring remote anchorages, charming small towns, and the hidden beauty of Bras d’Or Lake in Cape Breton Island. A true cruising boat life adventure! NEW VIDEOS EVERY SUNDAY! Please subscribe and share our videos - every bit of support is much...
Yay! My Portable AC Is Working Again! #boatlife #writerslife #japan
Hi, Lowell here from Pacific Solo and the Never Too Late Academy, aboard my Gib Sea 402 Wahine, moored in Buren Bay on Japan’s Amami Island. With one typhoon heading toward China (safe travels, friends) and another brewing for next week, I’m prepping Wahine before heading to the mainland for writin...
Into the Wind: Sailing East to Sint Maarten
We set sail from the British Virgin Islands, taking on one of the most challenging points of sail: east into the trades. As we make our way to Sint Maarten, we reflect on the many passages that have brought us to this point—and why it always seems like we’re heading against the grain. With our sigh...
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...
OFFICIALLY Back in The Bahamas! | Sailing Sunday Vlog 289
We’ve officially made it to the Bahamas! After months on land adjusting to life as new parents we’re finally back on board sailing to the Bahanas. We checked into Marsh Harbour here in the Abaco, Bahamas to clear customs and immigration to start our first cruising days as a family of four. From chec...