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.

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ROUGH Sail to Dominica But it’s WORTH IT E397
Wildly Intrepid Sailing

ROUGH Sail to Dominica But it’s WORTH IT E397

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...
More Than Just a Rock in the Middle of the Atlantic | S6 E02
Sailing with six

More Than Just a Rock in the Middle of the Atlantic | S6 E02

📨 Join our newsletter: 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...
Their First Sailboat Is an Island Packet 40
Lady K Sailing

Their First Sailboat Is an Island Packet 40

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 ...
Flying Across the Caribbean for Yabá’s Biggest Upgrade Yet — Sailing Yabá
Sailing Yabá

Flying Across the Caribbean for Yabá’s Biggest Upgrade Yet — Sailing Yabá

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,...
Exploring Herceg Novi, Montenegro | Catamaran Boat Servicing & Cruising Life
Sailing Clewless Crew

Exploring Herceg Novi, Montenegro | Catamaran Boat Servicing & Cruising Life

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 Most People Never Live Their Sailing Dream
Lady K Sailing

Why Most People Never Live Their Sailing Dream

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, ...
WE’RE BACK AT SEA! 🌴 San Blas, Boat Repairs & Insurance Update! Ep-235
Leading the Escapade

WE’RE BACK AT SEA! 🌴 San Blas, Boat Repairs & Insurance Update! Ep-235

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?
Lady K Sailing

Why Are Used Sailboats So Cheap in 2026?

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...
Hidden Hot Springs & Sailing life of a family in Guadeloupe E396
Wildly Intrepid Sailing

Hidden Hot Springs & Sailing life of a family in Guadeloupe E396

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...
Leaving Africa Behind | 11 Days Across the Atlantic | S6 E01
Sailing with six

Leaving Africa Behind | 11 Days Across the Atlantic | S6 E01

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: Old Town, Mussels & Wildfire Smoke
Sailing Clewless Crew

Sailing KOTOR Bay: Old Town, Mussels & Wildfire Smoke

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...
Sailing to Rio: Exploring Brazil’s Most Famous City — Sailing Yabá
Sailing Yabá

Sailing to Rio: Exploring Brazil’s Most Famous City — Sailing Yabá

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...
Italian coastal adventures: Ponza and Gaeta
Sailing Helios

Italian coastal adventures: Ponza and Gaeta

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...
Sicily to the Aeolians: field notes
Sailing Queen Lizzy

Sicily to the Aeolians: field notes

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'...
What Do You Do With All Your Boat Receipts?
Lady K Sailing

What Do You Do With All Your Boat Receipts?

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...
Two Versions of One Night🌙 Did She Fall 🫣 or Is There More? 🤔#sailing #lynettehooker #mystery
Lady K Sailing

Two Versions of One Night🌙 Did She Fall 🫣 or Is There More? 🤔#sailing #lynettehooker #mystery

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: Or Instagram:
Coast Guard ⚓ Seizes ‘Soulmate’ Boat ⛵ in Missing Woman Case 🔎 #mystery #lynettehooker #truecrime
Lady K Sailing

Coast Guard ⚓ Seizes ‘Soulmate’ Boat ⛵ in Missing Woman Case 🔎 #mystery #lynettehooker #truecrime

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: Or Instagram:
Are Catamarans a Waste of Money? | Hot Take Tuesday
Lady K Sailing

Are Catamarans a Waste of Money? | Hot Take Tuesday

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...
The Boating Industry Is About to Change!
Lady K Sailing

The Boating Industry Is About to Change!

Go to www.vesselbook.com 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: Or Instagram:
Back on the Water in Bocas del Toro… 🌴 Ep-234
Leading the Escapade

Back on the Water in Bocas del Toro… 🌴 Ep-234

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,...
True Crime Sailing – A Cruising Wife Vanishes in the Bahamas
Lady K Sailing

True Crime Sailing – A Cruising Wife Vanishes in the Bahamas

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 Started DIVING in the Caribbean! E395
Wildly Intrepid Sailing

Our 4-Year-Old Started DIVING in the Caribbean! E395

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
The Cruising Kiwis

PLANS CHANGE. THINGS GO WRONG

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
Sailing Clewless Crew

Sailing STUNNING Montenegro

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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