Watch Sailing & Boating Adventures Around the World – Page 2 of 11

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 25-48 of 248 results
First Sea Trial After 2 Years at the Dock!
Gone with the Wynns

First Sea Trial After 2 Years at the Dock!

After two years sitting still, we got this boat off the dock. But not before discovering why boats don’t like being ignored. Start 2026 with better sleep! Try Beam Dream: and use code WYNNS for up to 40% off - limited time only. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gea...
Our First Christmas Market (& A Thank You)
Gone with the Wynns

Our First Christmas Market (& A Thank You)

Merry Christmas and Happy Holidays! ☝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 (SFX, Templates & Presets): - 🎽GET YOUR SWAG ON: -------...
This Boat Sat for 2 Years… Does It Even Work?
Gone with the Wynns

This Boat Sat for 2 Years… Does It Even Work?

We Finally Found Out If Our Auction Boat Actually Works. 🎁 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: 📧EMAIL notifications, so you never miss a video🍦 ...
The Most Dangerous Ride of Our Lives: Baja 1000
Gone with the Wynns

The Most Dangerous Ride of Our Lives: Baja 1000

The Baja 1000 is approximately 1000 miles of endless possibilities for bad decisions. 🏎️ AG1 has their best offer EVER - subscribe with my link and you’ll unlock 7 free gifts worth $126 ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: ...
ROBBED! How We Were Targeted by Thieves
Gone with the Wynns

ROBBED! How We Were Targeted by Thieves

We’ve traveled for over a decade without anything like this ever happening… until now. Robbed in Amsterdam. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids. 2 Months...
We Won A $2M Boat At Auction
Gone with the Wynns

We Won A $2M Boat At Auction

We bought an Explorer Yacht on AUCTION! 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: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids. ...
New Boat, Baja 1000 & Sailing Antarctica!
Gone with the Wynns

New Boat, Baja 1000 & Sailing Antarctica!

BIG Adventures Ahead! Shop Beam’s Black Friday Sale! Get up to 50% off with my link: (limited time only!). No code needed - discount will auto apply at checkout! Sailing Antarctica! More about Captain Cathrine and our Expedition to Antarctica: Baja 1000 If you want to see the schedule and race m...
IT’S DECISION TIME! Choosing Our Explorer Yacht
Gone with the Wynns

IT’S DECISION TIME! Choosing Our Explorer Yacht

After six months, countless miles, and what feels like a hundred boats later… 🌊 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: 📧EMAIL notifications, so you ...
Owning a 103 Year Old Vessel: Dream or Madness?
Gone with the Wynns

Owning a 103 Year Old Vessel: Dream or Madness?

Buying a 100-Year-Old Wooden Boat! Head to to get a free AG1 welcome kit when you first subscribe! ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids. 2 Months Free: ...
The Ultimate Explorer Yacht Test
Gone with the Wynns

The Ultimate Explorer Yacht Test

The final test is here, and Mother Nature decided to show up.🌊 Stay salty! Get your free LMNT Sample Pack with any purchase at ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUS...
What It’s ACTUALLY Like, at Sea, on an Explorer Yacht
Gone with the Wynns

What It’s ACTUALLY Like, at Sea, on an Explorer Yacht

Life Aboard a Trawler. Want better sleep? Try our favorite sleep aid, Dream! Click and use code WYNNS for up to 35% off. Limited time only! ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a vi...
Our First Passage on an Explorer Yacht
Gone with the Wynns

Our First Passage on an Explorer Yacht

Alaska to Washington, Our First Adventure on a Trawler. 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: 📧EMAIL notifications, so you never miss a video🍦 🎶...
Million Dollar Yacht or Affordable Explorer?
Gone with the Wynns

Million Dollar Yacht or Affordable Explorer?

We check out two serious explorer yachts that actually make sense for what we're planning (high latitude). One is practically brand new (and way beyond what we can spend) and another that's older but feels like something we could actually make work. ☝Behind the Scenes, Gear Guides &...
Reality Check: Could This 1965 Classic Be Our Next Boat?
Gone with the Wynns

Reality Check: Could This 1965 Classic Be Our Next Boat?

Stay salty! Get your free LMNT Sample Pack with any purchase at Also try the new Flavor Lemonade Salt...it's "lemon squeezy" ☺️ Full Specs & Listing Information The Swan, a 1965 Feadship may not be our next boat but if it is perfect for you, the full specs and listings can be f...
Are We Buying Another Boat? (Life Update + What’s Next)
Gone with the Wynns

Are We Buying Another Boat? (Life Update + What’s Next)

The short answer is yes. We're sharing what’s been happening behind the scenes, the types of boats we’re considering (and why), and what this next chapter of our journey could look like. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK...
We Tried Taking Ourselves On Safari (no guides)
Gone with the Wynns

We Tried Taking Ourselves On Safari (no guides)

We thought, how hard could it be to take ourselves on an African safari? Turns out, when the trip starts with a dead battery, black smoke, and zero professional guidance, the answer is: pretty wild. From lions and giraffes to hippos and crocs, and even one very elusive leopard, we explored what fel...
INSIDE A LOCAL COMMUNITY IN UGANDA
Gone with the Wynns

INSIDE A LOCAL COMMUNITY IN UGANDA

We're back with part two of our Uganda series, and this one takes us even deeper into the country. Our destination? Teddy's home village in the Mindi district. A place where school happens under trees, bricks are made by hand, and everyone knows everyone. It felt like we were exploring t...
A Farm, A Friend, A Cup of Something UNEXPECTED
Gone with the Wynns

A Farm, A Friend, A Cup of Something UNEXPECTED

With skepticism in our mugs and curiosity on our tongues...🦈 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: 📧EMAIL notifications, so you never miss a video🍦...
This Village Has No Roads – Only Canals and Boats
Gone with the Wynns

This Village Has No Roads – Only Canals and Boats

Stay salty! Get your free LMNT Sample Pack with any purchase at Also try the new Limited-Time Flavor Lemonade Salt. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids....
ALASKA to PATAGONIA: Our First Look at an Explorer Yacht
Gone with the Wynns

ALASKA to PATAGONIA: Our First Look at an Explorer Yacht

From sails to steel, we’re exploring every option for an Alaska to Patagonia journey. Which means we need a vessel fit for pole to pole extreme conditions and all the heat in between. 🚢 Watch The First Yacht Tour With @NautiStyles Rico & Victoria: The Real Ship Listing with all the specs: ...
DIY Adventure Van – Our Stealth Base Camp
Gone with the Wynns

DIY Adventure Van – Our Stealth Base Camp

A stealthy van build to pair with our next boat home. Get 10% off beautiful tableware that will stay put no matter what kind of adventure you are on. Use code WYNNS 👉 ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notificat...
Sailing The Dreamiest Hybrid Electric Catamaran
Gone with the Wynns

Sailing The Dreamiest Hybrid Electric Catamaran

At 3.6 million this isn't just any catamaran, it's a fully loaded home and adventure base camp like nothing we've seen before. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a vid...
A Floating Commune for Sailors?
Gone with the Wynns

A Floating Commune for Sailors?

We kept hearing rumors about this sailing community in the Bahamas and it sounded a little too perfect.🦈 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: 📧EMA...
An Unexpected 3 Days In Türkiye
Gone with the Wynns

An Unexpected 3 Days In Türkiye

Istanbul wasn't on our radar but when a last minute invitation came, we couldn't say no. ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 📱Socials INSTAGRAM: FACEBOOK: 📧EMAIL notifications, so you never miss a video🍦 🎶 MUSIC for vids. 2 Months Free: ...
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