Watch Sailing & Boating Adventures Around the World

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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WE’RE TEARING HER APART 😳 The Rebuild Begins | S2.E206 | Sailing SV CUBA
Sailing SV CUBA

WE’RE TEARING HER APART 😳 The Rebuild Begins | S2.E206 | Sailing SV CUBA

After a devastating lightning strike, the rebuild of our sailboat finally begins… ⚡️😳 We’re tearing her apart, stripping her down, uncovering hidden damage, and taking the first steps toward bringing her back to life.⚡️ Boat life rebuild One step at a time. *Want to support us?" Patreon: Buy ...
These Waves Hit Harder Than Expected
Gone with the Wynns

These Waves Hit Harder Than Expected

A smooth sea never made a skilled sailor. Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & Vi...
This Is Not the England We Expected
Gone with the Wynns

This Is Not the England We Expected

Fossils, ghost villages, white cliffs and a coastline we never expected... Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & V...
Mom’s First Adventure Aboard Our Explorer Yacht
Gone with the Wynns

Mom’s First Adventure Aboard Our Explorer Yacht

Jason's mom finally joins us aboard our explorer yacht in England. 💦Stay Salty! Get your free LMNT Sample Pack with any purchase at The hardest part of this life isn't the weather, the logistics, or the constant maintenance. It's being far away from the people we love. ☝Behind the...
One Design Problem Is Limiting Our Entire Boat
Gone with the Wynns

One Design Problem Is Limiting Our Entire Boat

Our dinghy problem is bigger than it looks.🤔 Beam Dream is giving you early access to the Labor Day sale: up to 46% off for a limited time. Use the link in the description or Use code WYNNS at checkout! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikk...
We Had NO Choice… Someone Had to Leave the Boat FOREVER!🫤Ep.202
Sailing SV CUBA

We Had NO Choice… Someone Had to Leave the Boat FOREVER!🫤Ep.202

I left everything behind to live a completely different life on a sailboat.This week, things are not working out between everyone on board the best solution is to part ways. Get Out or Get Eaten! 😕 *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: PayPal:
We’ll Never Look at Honey the Same Again
Gone with the Wynns

We’ll Never Look at Honey the Same Again

We thought honey was simple. We were very wrong. 🐝 Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & Video Gear 📷 📱Socials ...
We Invited a Family to Live on Our Boat for a Month
Gone with the Wynns

We Invited a Family to Live on Our Boat for a Month

Two of us became six. Here's how that actually went. Head to to get a FREE AG1 Flavor Sampler and a FREE bottle of Vitamin D3+K2 in your Welcome Kit with your first AG1 subscription order ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓...
My SECRET Fear🫣 & The Pure Ocean Marine (Portable Watermaker) 💦 Ep.201
Sailing SV CUBA

My SECRET Fear🫣 & The Pure Ocean Marine (Portable Watermaker) 💦 Ep.201

Get 18% Off the GO45 using the discount code: SVcuba Check Out the GO45 at: #PureOceanMarine #PortableWatermaker #OffGridSailing #boatlife #desalination #watermaker *Want to support our Journey?" Patreon: Buy Salsa a Coffee☕🧡:
I Left Conventional Life to Chase Paradise by Sailboat – Ep200
Sailing SV CUBA

I Left Conventional Life to Chase Paradise by Sailboat – Ep200

I left everything behind to live a completely different life on a sailboat. This is my daily boat life routine — sailing to remote islands, anchoring in crystal-clear turquoise waters, and exploring paradise every single day. In this episode, I take you with me as I wake up in a new anchorage, exp...
Inside Our 50ft Aluminum Explorer Yacht
Gone with the Wynns

Inside Our 50ft Aluminum Explorer Yacht

Tour of our new Explorer Yacht. Stay Salty! Get your free LMNT Sample Pack with any purchase at ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧J...
Crossing the World’s Busiest Ocean Highway
Gone with the Wynns

Crossing the World’s Busiest Ocean Highway

The first true test of our new-to-us explorer yacht. 🌊 Beam Dream changed our sleep! Get up to 48% off sitewide right now with our exclusive code: WYNNS ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ 📷 Photo &...
A Different Kind of Boat Life
Gone with the Wynns

A Different Kind of Boat Life

Our first miles on the North Sea and a new chapter ahead.🌊 Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️ ...
CRITICAL ELECTRICAL FAILURE & A Rough Ride to the Outer Reef! (Ep. 189)
Sailing SV CUBA

CRITICAL ELECTRICAL FAILURE & A Rough Ride to the Outer Reef! (Ep. 189)

We knew something was wrong with our sailboat's electronics, but we couldn't track down the mystery issue. So, we decided to clear our heads the only way we know how—by taking a hell-fast, incredibly bumpy boat ride out to a stunning island on the outer reef! 🌊🏝️ *Want to support us?"...
The Last Thing Standing Between Us and Open Water
Gone with the Wynns

The Last Thing Standing Between Us and Open Water

The one test that had to work before we could finally leave the dock. 🦈 Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn More Gyro Specs: 🧰 Anchor, Chain, Tools and all the other gear 🛠️ ⚓️ Our Explorer Yacht ...
Stretched Too Far… What’s Next for SV CUBA? 😱 E.188
Sailing SV CUBA

Stretched Too Far… What’s Next for SV CUBA? 😱 E.188

After years of chasing horizons, crossing oceans, and sharing every step of our sailing journey, we have some emotional news to share. It's been an incredible journey so far—from offshore passages and island hopping to boat projects and repairs, cruising life, and unforgettable moments at sea. ...
Nothing Works on my Sailboat 😕 E.187
Sailing SV CUBA

Nothing Works on my Sailboat 😕 E.187

In this episode of my chaotic sailing life, I’m filming the continuing breakdown from my previous episode: what stopped working, what I’ve tried so far, weird symptoms, and all the things that keep going wrong. If you know anything about sailboat electrics, please drop your advice in the comments — ...
This Cost a Fortune… We Removed It Anyway
Gone with the Wynns

This Cost a Fortune… We Removed It Anyway

We've discovered a surprising number of things that made us stop and ask, "Why on earth was this installed?" Plus, we finally splash! We are back on the water! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yac...
Why I’m Going Underwater to Escape Boat Life? 😳 | E.186
Sailing SV CUBA

Why I’m Going Underwater to Escape Boat Life? 😳 | E.186

Why it's everything breaking today in the boat? *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wish List: PayPal:
We Thought We’d Never See These Again
Gone with the Wynns

We Thought We’d Never See These Again

A year after selling our last boat, we finally tied up one of the last loose ends... Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn If ...
600 Miles Across the Most Feared Ocean on Earth
Gone with the Wynns

600 Miles Across the Most Feared Ocean on Earth

Sailing from Antarctica to Argentina across the infamous Drake Passage. ⛵️🌊 Struggling with sleep? Try Dream and shop Beam’s Memorial Day sale—use + code WYNNS for up to 40% off! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⛵️More about S/V...
ZERO BOAT LIFE DRAMA | Sunshine & Sharks | E184 | Sailing SV CUBA
Sailing SV CUBA

ZERO BOAT LIFE DRAMA | Sunshine & Sharks | E184 | Sailing SV CUBA

No boat drama…Unexpected wildlife encounters, this is the kind of boat life we dream about. #sailing #BoatLife #LifeStyle *Want to support us?" Patreon: Buy Salsa a Coffee☕🧡: Amazon Wish List: PayPal:
We Didn’t Expect This in Antarctica
Gone with the Wynns

We Didn’t Expect This in Antarctica

Leopard seals, questionable decisions, and possibly the worst place in Antarctica to park a dinghy. Stay Salty! Get your free LMNT Sample Pack with any purchase at ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⛵️More about sailing Antarctic...
The Antarctica Most People Never Get to See
Gone with the Wynns

The Antarctica Most People Never Get to See

Exploring the world on a small boat vs a cruise ship always opens up a whole other side to a place. But that feeling is intensified here. Join The Curiosity Crew - ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⛵️More about sailing with Ice...
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