Watch Sailing & Boating Adventures Around the World tagged “Sail 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 992 results
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 https://www.drinkag1.com/gonewiththewynns and you’ll unlock 7 free gifts worth $126 https://www.gonewith...
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. https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 https://www.gonewiththewynns.co...
1500 Miles to Fiji through the ITCZ – Sailing Sweet Ruca [Ep. 192]
Sailing Sweet Ruca

1500 Miles to Fiji through the ITCZ – Sailing Sweet Ruca [Ep. 192]

Battling through the ITCZ (Inter Tropical Convergence Zone), we sail 1500+ miles from the Marshall Islands to beautiful Fiji. This is part one of our 12 day bluewater sailing voyage through some of the most remote parts of the pacific ocean. #sailing #sto...
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 https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷...
I Found a $25K Benetti Yacht for Sale… Here’s Why It’s So Cheap
Sailing Zingaro

I Found a $25K Benetti Yacht for Sale… Here’s Why It’s So Cheap

A Benetti yacht… for twenty-five thousand dollars?! This 61' Benetti steel sailing yacht, designed by Laurent Giles, is heading to auction — and on paper, it looks like the deal of the century. But is it really? In this livestream, I’ll break down e...
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: https://shopbeam.com/WYNNS (limited time only!). No code needed - discount will auto apply at checkout! Sailing Antarctica! More about Captain Cathrine and our Expediti...
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 https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides...
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 https://drinkag1.com/gonewiththewynns to get a free AG1 welcome kit when you first subscribe! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 https:...
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 https://shopbeam.com/WYNNS and use code WYNNS for up to 35% off. Limited time only! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Pho...
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 https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo &amp...
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. http...
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 https://www.drinkLMNT.com/GoneWithTheWynns. Also try the new Flavor Lemonade Salt...it's "lemon squeezy" ☺️ Full Specs & Listing Information The Swan, a 1965 Feadship may not be our ...
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. https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guide...
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 https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Pho...
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 https://www.drinkLMNT.com/GoneWithTheWynns. Also try the new Limited-Time Flavor Lemonade Salt. https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video ...
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 & Victori...
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 👉 https://silwy.de/wynns https://www.gonewiththewynns.com ☝Behind the Scenes, Gear ...
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. https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 https://www.gonew...
New Logo Reveal!! Designed by Karin Binz @MyYachtLogo | Sailing Sisu Leopard 45 Catamaran Chartering
Sailing Sisu

New Logo Reveal!! Designed by Karin Binz @MyYachtLogo | Sailing Sisu Leopard 45 Catamaran Chartering

We’re excited to unveil our brand new sailing logo! ⛵✨ Designed by the super talented Karin Binz @ myyachtlogo – a fellow sailor who really gets what we’re all about. Her creativity, attention to detail, and understanding of the sailing world ma...
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 https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind ...
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. https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guides & More 📷 Photo & Video Gear 📷 https://www.gonewiththewynns.com/photo-video-gear ...
OFFSHORE SAIL NORTH: no choice but to take it on the chin – Ep 237
Sailing Jibsea

OFFSHORE SAIL NORTH: no choice but to take it on the chin – Ep 237

We set sail from the British Virgin Islands on a major offshore passage marking the first leg of our journey north in our new to us custom aluminum expedition sailboat toward remote, high-latitude destinations. This episode is a raw and unfiltered view of ...
The Fastest Cat You’ve Never Heard Of (+full tour)
Gone with the Wynns
This Electric Boat Changes Everything…Or Does It?
Gone with the Wynns

This Electric Boat Changes Everything…Or Does It?

After two weeks of living aboard this unique electric sailboat, we’ve got thoughts. Go to https://surfshark.com/wynns or use code WYNNS at checkout to get 4 extra months of Surfshark VPN! https://www.gonewiththewynns.com ☝Behind the Scenes, Gear Guide...
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