Watch Sailing & Boating Adventures Around the World – Page 2 of 41
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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Is the Beneteau First 44.7 the perfect cruising sailboat for people who genuinely love to sail? In this Lady K Sailing review, we take a close look at a 2004 First 44.7 currently listed in Maryland for $120,000. Designed by Bruce Far...
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These boat maintenance mistakes can cost you thousands of dollars, damage expensive equipment, and make your boat much harder to sell. From forgetting when the engine oil was changed to losing maintenance receipts, missing warranty deadlines, and letting safety equipment expire, many boat owners rel...
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Is This Sweden's Best Kept Secret | 1985 Scanmar 35 | Full Tour
Join Canadian Ken and me as we tour one of the most intriguing—and least-known—bluewater cruising sailboats ever built. We had an absolute blast exploring this...
If you've ever wondered what the everyday looks like when you quit your job and live on a sailboat, this is it 😀
Last week, we began our sailing journey down Sardinia's stunning west coast as we head south towards Africa. With our time in Europe coming to an end, we're being forced t...
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The Shannon Shoalsailer 35 might be one of the strangest cruising sailboats ever built: a 35-foot sailboat with no conventional keel, no centerboard, no daggerboards, and only about 30 inches of draft. Designed by Shannon Y...
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A Newly Completed Traditional Yacht in 2026? | Eastsail All Weather 25 | Full Tour
Welcome back BoatFools Nation!
Today Captain Kew and I tour BLACK MAGIC, a newly completed Eastsail All Weather 25—a traditional fu...
#boatfoolssailing #capedory36 #bluewatersailing #atlanticcrossing #sailboattour
Six Boats. One Atlantic Dream. Why He Chose a Cape Dory 36.
Welcome back BoatFools Nation! This one is a little different—and exactly the kind of story we love.
Back in February, Andrew flew all the way from Norway t...
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The weather can be one of the hardest parts of living aboard full time... and this week, it reminded us exactly why 🌊
After com...
We have officially kicked off our liveaboard life for 2026! 🌍⛵
We’ve finally left the marina and our full-time sailing adventure aboard Rúna has officially begun!
In this episode, we leave the marina and set sail from northern Italy on our 11m catamaran, Rúna, and begin our 2026 Mediterranean sail...
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Our ‘New’ Sailboat Is Already Fighting Back | Morgan 384
Canadian Ken and I are back aboard our “new-to-us” Morgan 384 as we race to get her ready for charter season in Maine… but like every old sailboat, she has a few opinio...
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26 Feet, 2 Cabins & Only $5,400?! | 1977 Parker Dawson 26 Pocket Cruiser | Full Tour
As of 05/15/2026: SOLD
***Quick note: technically this boat has a swing keel, which is 1,100 lbs, and locks in the down ...
If you’re researching the Lagoon 450 bulkhead issue, wondering about Lagoon 450 structural problems, or asking “do Lagoon 450s break in half?” — this video breaks down everything you need to know. We cover forward bulkhead deformation on Lagoon catamarans, how common the issue actually is, which yea...
#boatfoolssailing #cheapboats #boattour #herreshoff #cheoylee #classicsailboat
Old Boat, Big Charm | 1968 Cheoy Lee Offshore 31 for $12.5K
In this episode of BoatFools Sailing, Canadian Ken and I travel to Bath, Maine — home of Bath Iron Works — to step aboard a beautifully cared-for 1968 Cheoy ...
Why would anyone choose a trimaran over a monohull? In this video, we compare the Dragonfly 36 trimaran vs a Beneteau Oceanis 40.1 to answer one of sailing’s biggest questions: are trimarans better than monohulls? We break down trimaran vs monohull pros and cons, including speed, stability, comfort,...
Why are whales sinking sailboats? Over the last few years, reports of orcas attacking sailboats have exploded across the sailing world, particularly off the coasts of Spain, Portugal, and the Strait of Gibraltar. Sailors have reported killer whales targeting rudders, disabling steering, and in some ...
Living on a sailboat sounds amazing… until reality sets in.
In this video, we talk honestly about why most people quit living on a sailboat. Not the romantic Instagram version. The real, day-to-day challenges that catch people off guard and slowly wear them down.
If you’re thinking about:
• living o...
Can you live on a sailboat if you’re not a sailor?
Yes. And it doesn’t have to be expensive, old, or uncomfortable.
In this video, we’re talking about the cheapest modern sailboats you can actually live on. Not performance boats. Not ocean-crossing yachts. Just modern, affordable, floating homes tha...
Can you really live on a sailboat for free?
Not the Instagram fantasy version — the real, practical version.
In this video, we break down how people actually live on sailboats for little to no monthly cost, using real systems that work in the real world. This isn’t about hacks or shortcuts. It’s ab...
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