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.

Showing 1-24 of 249 results
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’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 ⚓...
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 ⚓️ ...
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 ...
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...
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...
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...
We Sailed Into an Active Volcano…in Antarctica!
Gone with the Wynns

We Sailed Into an Active Volcano…in Antarctica!

Steaming beaches, penguins and an ending none of us saw coming! Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ⛵️More about sailing with Icebird Expeditions ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our...
Living on a Sailboat in Antarctica (Full Tour)
Gone with the Wynns

Living on a Sailboat in Antarctica (Full Tour)

Welcome aboard our home in Antarctica! Head to to get an AG1 Flavor Sampler and a bottle of Vitamin D3+K2 FREE in your Welcome Kit with your first AG1 subscription (a $72 value!) ⛵️More about Icebird Expeditions ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jas...
This Wasn’t How Antarctica Was Supposed to Start
Gone with the Wynns

This Wasn’t How Antarctica Was Supposed to Start

It really is about the journey as much as the destination. Get an exclusive 15% discount on Saily data plans! Use code WYNNS at checkout. Download Saily app or go to ⛵️More about Icebird Expeditions ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki...
We have to leave 😬 (but let the upgrades begin!)
Gone with the Wynns

We have to leave 😬 (but let the upgrades begin!)

It's time to go...but the boat isn't ready! Struggling with sleep? Dream changed the game for me. Visit and use code WYNNS for up to 40% off—limited time only! ☝Behind the Scenes, Gear Guides & More 🎬 Produced, Filmed and Edited by: Jason & Nikki Wynn ⚓️ Our Explorer Yacht ⚓️...
Is This Boat Ice Proof? We’re About to Find Out!
Gone with the Wynns

Is This Boat Ice Proof? We’re About to Find Out!

Our first time breaking ice with a boat! 🌎 Get an exclusive 15% discount on Saily data plans! Use Our 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 UN...
The Scariest Test On Our Boat Yet
Gone with the Wynns

The Scariest Test On Our Boat Yet

It’s the invisible killer of boats.⚡️ Stay salty! Get your free LMNT Sample Pack with any purchase at ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids. 2 Months Free: 🎨 Creative Assets for Vids (...
Our Boat is Stuck in Maritime Purgatory
Gone with the Wynns

Our Boat is Stuck in Maritime Purgatory

We’ve been keeping a secret… sort of. 🌊 Go to or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids. 2 Months Free: 🎨 Creative Ass...
Boat Life Below Freezing
Gone with the Wynns

Boat Life Below Freezing

Our first taste of winter boat life! If you’re struggling, consider therapy with our sponsor. Click for a discount on your first month of therapy. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids. 2...
Robbed…And It Forced Us To Simplify
Gone with the Wynns

Robbed…And It Forced Us To Simplify

A BIG shift in how we travel and film. Head to to get FREE AG1 & AGZ Travel Packs, Vitamin D3+K2, and an AG1 Welcome Kit when you first subscribe. 📷 Photo & Video Gear 📷 ☝Behind the Scenes, Gear Guides & More 📱Socials INSTAGRAM: FACEBOOK: 📧JOIN THE CREW🍦 🎶 MUSIC for vids...
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