Watch Sailing & Boating Adventures Around the World – Page 2 of 122

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 found a simple way to make boat life easier
A Life Awry Sailing

We found a simple way to make boat life easier

Living on a boat sounds pretty idyllic… until you need to do a grocery shop😅 We’ve been spending the last two weeks exploring the Keppel Islands, but with our next move coming up, it’s time to seriously restock the boat. The problem? We don’t have a car. That means anchoring close enough to a sup...
A Military Closure Forced Us To Stop
A Life Awry Sailing

A Military Closure Forced Us To Stop

Five weeks after leaving the dock in Brisbane, we're finally starting to find our rhythm as a family of four living aboard our sailboat. This week, an unexpected military closure means we're stuck in the stunning Keppel Islands for two weeks. At first, we weren't sure what we'd ...
Was that our Last Sail on Zatara? (+ big announcement! 📢)
Sailing Zatara

Was that our Last Sail on Zatara? (+ big announcement! 📢)

📶 Need cell data? Get an exclusive 15% discount on Saily data plans! Use code SAILINGZATARA at checkout. Download the Saily app or go to Interested in buying Zatara? You can learn all about our 2006 Privilege 585 catamaran throughout our 500 videos on YouTube, but this recent episode shares specif...
Squalls Sloths & Surf… But Something Is Changing.. | EP145 HD 1080P
Motherload sailing

Squalls Sloths & Surf… But Something Is Changing.. | EP145 HD 1080P

The last two weeks aboard the Motherload have been a little bit of everything. Squally weather, wild skies, plenty of surf, and finally… SLOTHS! 🦥 After all the chaos, uncertainty, boat projects, and miles traveled, that first real encounter with sloths was one of those moments that stopped us in ou...
Why does this make me Nervous
Sailing Miss Lone Star

Why does this make me Nervous

5% Discount Code: SAILINGMISSLONESTAR 👉 The MAGIC happens on the Daily Show 👉 Join the Inner Circle (Patreon) Get behind-the-scenes access, community, and perks: 👉 What we are working on right now We are rebuilding Houdini into a safer, more capable offshore boat with a focus on structural in...
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 ⚓...
Will Repair Work Ever Stop on Our Aluminium Catamaran??
Sailing Dawn Hunters

Will Repair Work Ever Stop on Our Aluminium Catamaran??

Dawn Hunters documents full-time life at sea, offshore cruising, vessel systems, refits, engineering, and the realities of operating sailing catamarans beyond conventional cruising routes. After years of living aboard, modifying, testing, and operating different vessels, we are now applying that ex...
I finally discovered what makes me sea sick |  Family of 4 living aboard
A Life Awry Sailing

I finally discovered what makes me sea sick | Family of 4 living aboard

Some days on the water remind us exactly why we chose this life. This week, we set off before sunrise on a 70-nautical-mile sail to our next destination. With calm weather, a beautiful day ahead, and 13 hours on the water, we settle in for another family adventure. Like any journey, there are a fe...
Why We AREN’T Afraid of Sharks!
Sailing Zatara

Why We AREN’T Afraid of Sharks!

Go to or use code ZATARA at checkout to get 4 extra months of Surfshark VPN! Learn More About Zatara’s Highfield Sport 420 expedition dinghy: Want to cruise but not sure where to start? Keith breaks it all down here: This is the stuff we use every day—on and off the boat. Zatara merch, camer...
We Didn’t Know If We Could Keep Going…  | EP144 HD 1080P
Motherload sailing

We Didn’t Know If We Could Keep Going… | EP144 HD 1080P

For the past few weeks, we’ve questioned everything. After disappointment, uncertainty, and wondering if Motherload Sailing had reached its end, we honestly weren’t sure what came next. Sometimes life doesn’t give you a clear course—it simply asks you to keep moving forward. Then something unexpecte...
Boat Owners Nightmare
Sailing Miss Lone Star

Boat Owners Nightmare

The MAGIC happens on the Daily Show 👉 Join the Inner Circle (Patreon) Get behind-the-scenes access, community, and perks: 👉 You can follow the full roadmap and see exactly what we are doing here: 👉 Support the project / partner with us If you are a brand that wants to be part of this build o...
Why We Chose Boat Life (And What It Really Costs)
A Life Awry Sailing

Why We Chose Boat Life (And What It Really Costs)

Why did we choose a boat over a house? And what does it really cost to live on a sailboat? These are two of the questions we get asked the most, so in this week's episode we're sharing the honest answers. When we first bought our sailboat back in 2019, it was all about adventure. But ove...
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...
We QUIT Our Office Jobs To Buy A Boat! – Here’s What It’s Really Like | S2 – EP8
The Runa Life

We QUIT Our Office Jobs To Buy A Boat! – Here’s What It’s Really Like | S2 – EP8

*Learn more about our Orca Chart Plotter: If you've ever wondered what the everyday looks like when you quit your job and live on a sailboat, this is it 😀 We quit our office jobs in 2025 to chase a dream of sailing the world. Now we live, work remotely, and adventure full-time aboard Rúna, o...
We (almost) Bought an Island! 🏝️
Sailing Zatara

We (almost) Bought an Island! 🏝️

Learn More About Zatara's Highfield Sport 420 expedition dinghy: Want to cruise but not sure where to start? Keith breaks it all down here: This is the stuff we use every day—on and off the boat. Zatara merch, camera gear, Keith’s favorite tools, and boat life essentials! 👇 Happy Sailin...
Showering in the Rain 🌧️ The Unexpected Perks of Boat Life | EP.190
Sailing SV CUBA

Showering in the Rain 🌧️ The Unexpected Perks of Boat Life | EP.190

In this Episode I experience one of the simple pleasures that makes full-time sailing so rewarding. Fresh rainwater becomes the perfect shower as I embrace the unexpected perks of living off-grid on a sailboat. It's moments like these that remind me why I chose this incredible lifestyle. *Want...
We’ve Reached Our Breaking Point… What Happens Next..? | EP143 HD 1080P
Motherload sailing

We’ve Reached Our Breaking Point… What Happens Next..? | EP143 HD 1080P

Friends arrive in paradise, the waves are firing, and it’s Mom’s birthday—a recipe for unforgettable memories. But behind every smile is a reality we’ve struggled to hide. Living aboard with five growing boys isn’t always sunsets and anchorages. The pressure of parenting, maintaining a boat, creatin...
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 &...
Same Beach 10 years Later
Sailing Miss Lone Star

Same Beach 10 years Later

5% Discount Code: SAILINGMISSLONESTAR 👉 The MAGIC happens on the Daily Show 👉 Join the Inner Circle (Patreon) Get behind-the-scenes access, community, and perks: 👉 What we are working on right now We are rebuilding Houdini into a safer, more capable offshore boat with a focus on structural int...
FINALLY – BIG NEWS – Announcement from Dawn Hunters!
Sailing Dawn Hunters

FINALLY – BIG NEWS – Announcement from Dawn Hunters!

Dawn Hunters documents full-time life at sea, offshore cruising, vessel systems, refits, engineering, and the realities of operating sailing catamarans beyond conventional cruising routes. After years of living aboard, modifying, testing, and operating different vessels, we are now applying that ex...
We dreamed of this life but its harder than we expected
A Life Awry Sailing

We dreamed of this life but its harder than we expected

Life on a sailboat isn't always sunshine and perfect anchorages. This week we're anchored at Pancake Creek, where we set off on a family walk to the lighthouse before the weather has other plans. After a few days stuck onboard with two young kids, we start questioning whether this lifesty...
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 ⚓️ ...
SSL775 ~ Pablo Escobar’s ABANDONED MANSION..?
Captain Rick Moore

SSL775 ~ Pablo Escobar’s ABANDONED MANSION..?

SSL775 ~ Pablo Escobar's ABANDONED MANSION..? Hidden in the turquoise waters of Colombia’s Rosario Islands sits a crumbling white mansion slowly being swallowed by the jungle. Locals have whispered for decades that it once belonged to Pablo Escobar — his secret Caribbean hideaway. We took the d...
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