Watch Sailing & Boating Adventures Around the World – Page 2 of 111
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.
We say goodbye to Guadeloupe and set sail for Dominica, but it definitely isn't the smooth Caribbean sail we were hoping for!
The day starts with a bad feeling in my gut before we head out into a rough, lumpy sea for the crossing to Dominica. 🌧️⛵ It isn't our most comfortable passage, but...
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After 11 days at sea, St Helena felt like the perfect place to stop, reset and catch our breath.
But this tiny island in the middle of the South Atlantic turned out to be far more than just a convenient stopover.
We explored Jamestown, tackled Jacob’s Ladder far too many tim...
Would you buy an Island Packet 40 before you even knew how to sail? M and Nick did exactly that. With zero sailing experience, they skipped the typical starter boat and jumped straight into owning a serious 40-foot bluewater cruising sailboat.
In this episode of Small Channel Sunday, we talk about ...
Episode #326 | Flying to Barbados
To get Yabá ready for the next leg of our journey up the coast, it’s time for a massive upgrade: a brand-new sail wardrobe. But getting four heavy sails back to the boat means leaving Rio behind, making a pitstop in Arraial do Cabo to leave the boat in good hands,...
Hi and welcome, we are John and Sharon a mid 50's retired couple who brought a boat to live on and are currently sailing in the mediterranean.
Follow in real time:
Watch here to see the how we got the boat ready for this adventure:
Here you will be able to see how we navigated Greece:
We...
Why do most people never live their sailing dream? It isn’t because sailing is impossible—it’s because they keep waiting for more money, more experience, the perfect sailboat, or the perfect time. Whether you’re interested in sailing for beginners, buying your first used sailboat, learning to sail, ...
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...
Why are used sailboats so cheap in 2026? The used sailboat market has changed dramatically since the pandemic buying boom. Boats are sitting longer, asking prices are dropping, and many buyers are making offers thousands of dollars below list price. In this Lady K Sailing episode, we explore whether...
Sailing Guadeloupe with the family ⛵ Another beautiful stretch of Caribbean cruising!
We start out anchored in Malendure, where it’s time to tackle one of the less glamorous parts of boat life — the grocery run! With the boat stocked up, we jump into the clear Caribbean water for another incredible...
Season 6 starts here! 🌊⛵
After an incredible season in South Africa, it’s time to point Happy Days west and head out into the South Atlantic. Our next stop: the tiny, remote island of St Helena — 1,650 nautical miles and 11 days at sea.
And this passage gives us a little bit of everything… a foggy ...
Sailing Kotor Bay takes an unexpected turn as we explore Kotor Old Town, enjoy fresh mussels near Perast and visit the iconic Our Lady of the Rocks. But after saying goodbye to family, wildfire smoke and ash force us to move anchorages around Montenegro’s spectacular Bay of Kotor.
From catamaran li...
Saying goodbye to Lucas after weeks on board, but the crew swap is instant. Gui is back on Yabá! After a final trek through the jungle to the white sands of Lopes Mendes in Ilha Grande, we run our pre-departure engine checks and set a course straight for Rio de Janeiro.
Passing through the colonial...
We’re back in Ponza after sailing across from Sardinia. The island is as pretty as we remembered — a colourful Italian seaside town with a long and surprising history — and we have a few quiet days before Richard’s youngest son, Oakley, joins us on his European holiday.
The forecast, however, has ot...
Stromboli puts on fireworks every night, free of charge — very generous for a volcano. But don't forget the other islands out here!
Salina made us swap ambition for capers. No regrets.
Lipari has my husband convinced every stone is "probably Roman." Statistically, sometimes he'...
Where do you keep all your boat receipts, manuals, registration documents, maintenance records and paperwork?
Owning a sailboat or powerboat means accumulating an incredible amount of documentation. Receipts for marine electronics, batteries and repairs. Owner’s manuals for equipment. Boat registrat...
Lady K Swag!!! Right here:
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Lady K Swag!!! Right here:
Need a consult? Click here to drop a message:
Want to help support Lady K Sailing? Click here to become a Patron:
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Are catamarans actually worth the money, or have cruising sailors convinced themselves they need a floating luxury condo? In this Hot Take Tuesday, we’re looking at the real cost of cruising catamarans, whether most sailors actually need one, and why a much cheaper monohull can often do the exact sa...
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Lady K Swag!!! Right here:
Need a consult? Click here to drop a message:
Want to help support Lady K Sailing? Click here to become a Patron:
Or here to make a one time donation:
Follow Lady K on Facebook:
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We’ve been itching to get back out exploring, and this time we’ve got a new toy to see the adventure from a whole different perspective! 🚁
In this episode, we take the Antigravity A1 out for its first real adventure. After learning the basics back in the boatyard, we head to Bocas del Toro, Panama,...
A true crime sailing mystery in the Bahamas has left the cruising community with more questions than answers. In April 2026, sailor Lynette Hooker disappeared while cruising the Abacos aboard the sailboat *Soulmate* with her husband, Brian Hooker. What was first described as a tragic man-overboard a...
Our 4-year-old Coral is taking her underwater adventures to a whole new level! 🤿🌊
We explore the incredible Réserve Cousteau in Guadeloupe, where the water is crystal clear, the reef is full of life, and Coral starts diving below the surface all on her own. Watching her confidence grow underwater a...
PLANS CHANGE. THINGS GO WRONG
Sometimes you put a hole in your boat, races don't go your way, and whole course of life changes.This isn't an episode about a disaster; it's about how a family responds when things doesn't go to plan.
This week we continue our Caribbean sailing ad...
Sailing STUNNING Montenegro takes a wild turn as strong winds drag our anchor, we explore historic Budva, enjoy a restaurant mooring in Bigova Bay, and battle the crowds at the famous Blue Cave. We then head into spectacular Kotor Bay—plus fishing, provisioning and life aboard with Cleo.
#SailingMo...
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