Watch Sailing & Boating Adventures Around the World – Page 4 of 26

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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Boat Life: It’s Dirty… and She’s Just Not Into It | Ep.141
Sailing SV CUBA

Boat Life: It’s Dirty… and She’s Just Not Into It | Ep.141

It's a dirty situation—literally, the vibe is off, and she’s just not feeling it. In this Sailing Episode we show what life really looks like behind the dreamy sunset shots. Subscribe for weekly sailing life—raw, real, and unfiltered. #boatlife *Want to support us?" Patreon: Buy Salsa a ...
The Drunken Sailors Bar | Best Place To Prep, Cook & Eat The Fish We Caught In Mindelo | S6 Epsd 113
Winded Voyage Sailing

The Drunken Sailors Bar | Best Place To Prep, Cook & Eat The Fish We Caught In Mindelo | S6 Epsd 113

#sailing #sailinglifestyle #windedvoyage #adventure #africa #caboverde We caught a huge Whaoo tuna with our friend Jose. We then brought it to his bar, The Drunken Sailor's Bar, where he prepared it for us drunken sailors and merry wenches to enjoy. Jose on his boat Vasco de Gama offers the ful...
Catching A Huge Wahoo In Cabo Verde | The Best Place To Sport Fish & Not Always Easy | S6 Epsd 112
Winded Voyage Sailing

Catching A Huge Wahoo In Cabo Verde | The Best Place To Sport Fish & Not Always Easy | S6 Epsd 112

#sailing #sailinglifestyle #adventure #windedvoyage #fishing #africa #caboverde Cabo Verde Africa is reputed to be one of the best places for sport fishing. The annual Blue Marlin World Championship has been won here on many occasions. Our friend Jose took us out to test our fishing skills. And wha...
San Blas at Last: A Sailors Dream Years in the Making | Sailing Sitka Ep 163
Sailing Sitka

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...
Pirates Of Cabo Verde | Some Of The Colorful Characters I Met In Mindelo, Sao Vicente | S6 Epsd 110
Winded Voyage Sailing

Pirates Of Cabo Verde | Some Of The Colorful Characters I Met In Mindelo, Sao Vicente | S6 Epsd 110

#sailing #sailinglifestyle #adventure #windedvoyage #africa #caboverde Some say it’s The Best Sailing Channel on YouTube! Agree or disagree, make your voice heard. Subscribe, like, dislike, or comment. Mindelo, Sao Vicente. This is the home of real pirates of Cabo Verde. I’ve met the most interesti...
Boat Life Unfiltered: The Mission FAILED… Here’s The DIRTY Secret | Ep.139
Sailing SV CUBA

Boat Life Unfiltered: The Mission FAILED… Here’s The DIRTY Secret | Ep.139

You Wanna know the Dirty Secret after the failure? Join us this week in another episode of boat life unfiltered #boatlife #sailing *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wish List: PayPal:
Why We Anchored In The Rolliest Anchorage Yet [Ep. 179]
Sailing Sweet Ruca

Why We Anchored In The Rolliest Anchorage Yet [Ep. 179]

In this episode, we anchor in the rolliest anchorage we’ve encountered yet. With unpredictable conditions and tricky navigation, will our decision pay off? Join us as we face the challenges of the North Pacific and adapt on the fly! Plus, an impromptu man overboard drill keeps us on our toes. #sail...
Fishing With One Of The Best Legendary Sports Fisherman In Cabo Verde Africa | S6 Epsd 109
Winded Voyage Sailing

Fishing With One Of The Best Legendary Sports Fisherman In Cabo Verde Africa | S6 Epsd 109

#sailing #sailinglifestyle #adventure #caboverde #windedvoyage Somewhere out there is one of the most prize winning fish in the world. The Blue Marlin. Here in Cabo Verde world champion fishermen seek the great beast that can win them a million dollar prize. 00:00 Intro 00:25 Band of madafakas 03:...
UNFILTERED Boat Life on the Most ISOLATED Islands of the Caribbean | Ep.138
Sailing SV CUBA

UNFILTERED Boat Life on the Most ISOLATED Islands of the Caribbean | Ep.138

This is why I love Sailing Around The World. Join us in our latest sailing episode as we share a glimpse into our life at sea and exactly why we love sailing in tropical, crystal-clear waters! Like & subscribe to help us upgrade our editing gear and bring you even more epic adventures. Patreo...
Boat Life ⛵ She needs to Catch her Own Food! 🐟 Ep. 137
Sailing SV CUBA

Boat Life ⛵ She needs to Catch her Own Food! 🐟 Ep. 137

This is what boat life is all about! In this episode you get to see the real life of sailing around the world and how we live full time and living off-grid We're sailing around the world, and with your support, we will fund better cameras, the internet to upload videos, and of course, the occa...
Tried To Cross The Atlantic With Pregnant Wife, Dog & Cat | Sailor Quentin’s Story | S6 Epsd 107
Winded Voyage Sailing

Tried To Cross The Atlantic With Pregnant Wife, Dog & Cat | Sailor Quentin’s Story | S6 Epsd 107

#sailing #sailinglifestyle #adventure #windedvoyage #africa #caboverde Sailor Quentin has been sailing the world for more than a decade alone. But in the last year he met his girlfriend, adopted a cat and a dog in Morocco. Then decided to sail across the Atlantic from Cabo Verde. His girlfriend was ...
In search of The Last True Sailors of the Caribbean | Epic Journey (E.136)
Sailing SV CUBA

In search of The Last True Sailors of the Caribbean | Epic Journey (E.136)

Join us on an epic journey across the Caribbean as we track down the last true sailors—masters of the sea, tradition, and adventure. Don't miss. Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discovering ne...
Proof Of Maintenance | Meeting Strict Swiss Standards To Fly The Swiss Flag On My Boat | S6 Epsd 106
Winded Voyage Sailing

Proof Of Maintenance | Meeting Strict Swiss Standards To Fly The Swiss Flag On My Boat | S6 Epsd 106

#sailing #sailinglifestyle #africa #windedvoyage #caboverde Having a boat registered in Switzerland requires a general inspection to meet strict standards every 3 years to ensure the boat is seaworthy. It is to ensure and prove the boat is fully seaworthy. Not a bad idea, as I see countless boats th...
🌊 Living the Ocean Nomad Life – Discovering a Hidden Island Paradise! 🏝️✨ E.135
Sailing SV CUBA

🌊 Living the Ocean Nomad Life – Discovering a Hidden Island Paradise! 🏝️✨ E.135

Join me on an epic adventure as I embrace the ocean nomad life, sailing to a hidden island paradise! 🏝️🌊 Crystal-clear waters, untouched beauty, and pure freedom. Let’s explore! 🚤✨ Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from co...
Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158
Sailing Sitka

Final prep & nerves before our Panama Canal transit (real talk and costs $) | Sailing Sitka Ep 158

Jay and Kenna share some real thoughts and info as they prepare to transit the Panama Canal from the pacific to the Atlantic. But not before they enjoy some time enjoying the city life in Casco Viejo. Thanks for watching and subscribe if you enjoy. Stay tuned for next episode as it will be the one w...
Hear Why This Pro American Skipper Got Stuck In Cabo Verde Africa | Meet Captain Matt | S6 Epsd 105
Winded Voyage Sailing

Hear Why This Pro American Skipper Got Stuck In Cabo Verde Africa | Meet Captain Matt | S6 Epsd 105

#sailing #sailinglifestyle #adventure #windedvoyage #caboverde Meet Captain Matt and hear why he got stuck in Mindelo. In short he and crew set off to cross the Atlantic Ocean from Sao Vicente island into the fierce Sao Vicente canal and shredded their Genoa sail. It's a great sailing story. 0...
We Sailed to the Most Unexplored Island in the Caribbean – THE WILD QUEEN 🌋🩵E.134
Sailing SV CUBA

We Sailed to the Most Unexplored Island in the Caribbean – THE WILD QUEEN 🌋🩵E.134

Secure your privacy with Surfshark! Go to for an extra 4 months Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country to country discovering new adventures. *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wis...
Paella De Piratas & More | How We Sailors Live & Work In Cabo Verde Africa | S6 Epsd 104
Winded Voyage Sailing

Paella De Piratas & More | How We Sailors Live & Work In Cabo Verde Africa | S6 Epsd 104

#sailing #sailinglifestyle #adventure #windedvoyage #africa #caboverde Jose, long time sailor invited us to his place where he made his famous dipping sauce. Peppers onion, garlic and olive oil. Then, the secret is to drop a piece of sizzling coal in it. Gives an amazing charred taste. Then he gave...
Sailing to a remote, timeless village on Panama’s pacific coast | Sailing Sitka Ep 156
Sailing Sitka

Sailing to a remote, timeless village on Panama’s pacific coast | Sailing Sitka Ep 156

Jay and Kenna sail further into Panamanian waters only to discover a hidden gem of a village which was completely stuck in time. Join us on this special 3 year anniversary episode as we sail to Bahia Honda on Panama's pacific coast and learn to live slowly as we discovery the simplicity and bea...
Winter In Mindelo | How I Live & Work On My Sailboat In Cabo Verde Africa | S6 Epsd 103
Winded Voyage Sailing

Winter In Mindelo | How I Live & Work On My Sailboat In Cabo Verde Africa | S6 Epsd 103

#sailing #sailinglifestyle #adventure #windedvoyage #caboverde #africa Winter here is mostly constant strong winds coming down from the north. It can go on for days, weeks. Living aboard one’s floating home, you are very concerned with the wind pushing your boat around. As well as tide and swell whi...
Unexpected Challenges of Living on a Boat😝E.133
Sailing SV CUBA

Unexpected Challenges of Living on a Boat😝E.133

Living on a boat can be idyllic, but it also comes with unexpected challenges. This video explores some surprising hurdles faced by those who choose to live life on the water. Follow us every week in our real life sailing adventure, as we live off grid, sail from place to place, travel from country...
Sailing to Panama | Sailing Sitka Ep 155
Sailing Sitka

Sailing to Panama | Sailing Sitka Ep 155

In this video of sailing sitka, jay and Kenna sail to their first port in Panama from Golfito, Costa Rica. They anchor in front of a desolate little island consisting of nothing but tall standing palm trees and white sandy beaches. Thanks for watching and subscribe if you do!
The Simple Pleasures Of Living Aboard | How I Live & Work In Mindelo Cabo Verde Africa | S6 Epsd 102
Winded Voyage Sailing

The Simple Pleasures Of Living Aboard | How I Live & Work In Mindelo Cabo Verde Africa | S6 Epsd 102

#sailing #sailinglifestyle #windedvoyage #caboverde #africa That’s me there. Living the sailor’s life. Here in Mindelo. On my boat Galopin. I’m waiting for better weather and my crew before setting out. And I got a few things to fix on Galopin. And there's always something wrong. The simple ple...
I Couldn’t Resist Them | How I Spent My 64th Birthday In Mindelo, Cabo Verde Africa | S6 Epsd 101
Winded Voyage Sailing

I Couldn’t Resist Them | How I Spent My 64th Birthday In Mindelo, Cabo Verde Africa | S6 Epsd 101

#sailing #sailinglifestyle #windedvoyage #africa #caboverde Having my birthday mid-January, it’s too close to end of year festivities for me to partying so soon. As well it would be my 64th birthday. Not an age I enjoy announcing loudly. But this is Mindelo, Cabo Verde. Where things are very differe...
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