Watch Sailing & Boating Adventures Around the World – Page 5 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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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...
Our FIRST time SAILING in the Mediterranean Sea! S3 Ep.2
Good Deeds Sailing

Our FIRST time SAILING in the Mediterranean Sea! S3 Ep.2

We leave Port Saint Louis for a first sail out into the Med. Stopping over at Isles de Frioul where we go sightseeing before setting sail once again to a very rolly anchorage at Bandol Bay. Thank you to all our subscribers, our lovely Good Deeders :) Please like, share, comment, we love your feedba...
Journey to the most protected bay in Costa Rica | Sailing Sitka Ep 153
Sailing Sitka

Journey to the most protected bay in Costa Rica | Sailing Sitka Ep 153

In this episode of Sailing Sitka, Jay and Kenna sail the squally and sloppy seas from Quepos to Golfito, down the pacific costa of Costa Rica. After having numerous encounters with rolley anchorages, we finally make landfall in a bay that is often mistaken for a lake, thats how protected it is. Some...
Boat Life in Caribbean Islands🏄‍♀️ She’s Having All The FUN! 🤪 E.132
Sailing SV CUBA

Boat Life in Caribbean Islands🏄‍♀️ She’s Having All The FUN! 🤪 E.132

Join us for the epic final episode on this stunning island! From crazy boat life fun to unexpected blasts, we end the adventure with a bang! Don’t miss it!" Ps: I think she is having all the fun... Follow us every week in our real life sailing adventure, as we live off grid, sail from place to...
The real ups and downs of budget cruising | Sailing Sitka Ep 152
Sailing Sitka

The real ups and downs of budget cruising | Sailing Sitka Ep 152

Jay and Kenna sailed off from Victoria BC, Canada two years ago and have been sailing south ever since. Now, in the luscious lands of Costa Rica, they experience both the highs and lows that come with sailing and cruising offshore.Thank you for watching and subscribe if you enjoy!
I Messed Up! The Friendly Island – E.131 ⛵  Sailing SV CUBA
Sailing SV CUBA

I Messed Up! The Friendly Island – E.131 ⛵ Sailing SV CUBA

I messed up and if I could turn back time I would! Wonder what real life aboard a 46ft sailboat feels like? Here is how we live Off Grid on the Ocean and travel. We give you an insight into our daily life adventures aboard our sailboat. This week we are looking for a place that time seems to have ...
World’s Most Festive City | Holidays In Sao Vicente, Cabo Verde | A Sailors Perspective |S6 Epsd 99
Winded Voyage Sailing

World’s Most Festive City | Holidays In Sao Vicente, Cabo Verde | A Sailors Perspective |S6 Epsd 99

#sailing #sailinglifestyle #windedvoyage #caboverde #africa In all my travels, I have never been to a more festive place. Nowhere else will you find such an appetite to party. New Year's celebrations lasted for four nights. And this was the final night to bring in the New Year. It started with ...
It’s a Deja Vu Anchorage Ep160
Sailing Intermission

It’s a Deja Vu Anchorage Ep160

As we sat comfortably in the cockpit of our sailboat, a glass of wine in hand, relaxing and enjoying the breathtaking view. The air is a little crisp, as we watch fast-flying birds cut through the wind, their graceful movements adding to the sense of tranquility. Inside the VIP head, a new teak ba...
Getting Tattooed & Partying New Year’s In Mindelo | Holidays In Sao Vicente Cabo Verde | S6 Epsd 98
Winded Voyage Sailing

Getting Tattooed & Partying New Year’s In Mindelo | Holidays In Sao Vicente Cabo Verde | S6 Epsd 98

#sailing #sailinglifestyle #adventure #windedvoyage #africa #caboverde Yes, I got an anchor tattoo. Which symbolizes or says I sailed across the Atlantic Ocean. Which I accomplished a couple of years ago. I’ve been wanting to do that for a while now and finally did it after a bumped into local tatt...
THIS is why we sail offshore. | Sailing Sitka Ep 150
Sailing Sitka

THIS is why we sail offshore. | Sailing Sitka Ep 150

In this episode of sailing sitka, we sailed to Bahía Ballena here on the pacific side of Costa Rica. After some squally and rough seas, we were more than grateful to be anchored in such a postcard worthy anchorage. It really puts it into perspective exactly why sailors sail offshore... to arrive and...
Best Cape Verde Sailing Vacation | Scooters Beaches Bars & Boats Sao Vicente No Stress | S6 Epsd 97
Winded Voyage Sailing

Best Cape Verde Sailing Vacation | Scooters Beaches Bars & Boats Sao Vicente No Stress | S6 Epsd 97

#sailing #sailinglifestyle #windedvoyage #adventure #africa #caboverde We only scooted half way around the island. There's more to see, like beaches and bars. Boats coming in and out. And the dry mist called Bruma Seca. All part of the no stress life in Cabo Verde. Some say it’s The Best Saili...
I Love Screwing Ep158
Sailing Intermission

I Love Screwing Ep158

Anchored, cummins, jerry cans, screwing, dancing, fuel, diesel. We are still anchored. Started to go out, the engine died and ended up being towed back to the same anchorage we were at previously. Steve has done some diagnostics and we’re making progress on fixing the issue. Using the time to do so...
Best Cape Verde Sailing Vacation | Cruising Sao Vicente Island On Rented Scooters | S6 Epsd 96
Winded Voyage Sailing

Best Cape Verde Sailing Vacation | Cruising Sao Vicente Island On Rented Scooters | S6 Epsd 96

#sailing #sailinglifestyle #scootering #windedvoyage #sãovicente #caboverde One of the best ways to cruise around Sao Vicente Island is by scooter. They can be rented in Mindelo from several rental outlets, such as Djambai Tours, for under 30 bucks. We scooted up to the highest mountain and down to ...
Getting our boat ready for our next offshore passage in Costa Rica! Sailing Sitka Ep 148
Sailing Sitka

Getting our boat ready for our next offshore passage in Costa Rica! Sailing Sitka Ep 148

On this episode of Sailing Sitka, we get our Cheoylee sailboat offshore ready by provisioning fr food, water, fuel and some extra fixings by making do with what we got. This is the reality of cruising sometimes and making sure your boat is ready to hit the high seas. Subscribe to join the journey an...
Best Cape Verde Sailing Vacation | ARC Departure | Glorious Sailing To Sao Vicente | S6 Epsd 95
Winded Voyage Sailing

Best Cape Verde Sailing Vacation | ARC Departure | Glorious Sailing To Sao Vicente | S6 Epsd 95

#sailing #sailinglifestyle #adventure #windedvoyage #africa #caboverde Hundreds of sailors were in Mindelo, Cabo Verde before sailing out across the Atlantic to the Caribbean. A yearly event that bring sailors from all over to Mindelo for a few days to repair and provision for their journey. Dan an...
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