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

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 25-32 of 32 results
The Start of Our Next Chapter
Gone with the Wynns

The Start of Our Next Chapter

New boat, new chapter, and all the nerves that come with it. 🛥️ 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: 🎨...
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: -------...
My Tiny Hometown
Gone with the Wynns

My Tiny Hometown

It’s been a long time since we’ve taken a road trip, much less gone "home".  And for the first time, Nikki is taking you home to meet the family. See her childhood hometown and our ride around the USA. #VanLife JOIN OUR SAILING CREW ⛵ MORE DEETS on the BLOG post: Nikki's Sister:...
Gone With The Wynns Q&A: Patreon Crew, Future RV Plans, and Dealing With Expectations.
Sailing Ruby Rose

Gone With The Wynns Q&A: Patreon Crew, Future RV Plans, and Dealing With Expectations.

Okay, so first of all, I apologise for the audio in this video. There was a lot of background hull slap which the microphone picked up, so trying to reduce that while still keeping our voices sounding natural was a challenge for me. Anyway, onto the Q&A! Huge thankyou to our Patrons for submit...
A Brutally Honest Sundowner with Mom || Sailing with Family Q&A
Gone with the Wynns

A Brutally Honest Sundowner with Mom || Sailing with Family Q&A

Before Jason’s mom said goodbye in Tahiti, we sat her down, gave her some beers and asked YOUR burning questions. There's WAAAAYYYYYYY more on our website: We curated the questions from Instagram, Facebook and of course from our Patrons. We really only gave her two rules: Answer honestly and...
Gone With The Wynns 2.0
Gone with the Wynns

Gone With The Wynns 2.0

It's been over 4 years since we created a new "about us" or "Adventure" video. To say the task is daunting would be a complete understatement. But to go back through 6 years of videos is an epic adventure of it's own. It's like the video editing equivalent of cl...
The Wynns make salsa with Caleb and Milo
Gone with the Wynns

The Wynns make salsa with Caleb and Milo

If you know the Wynns then you know they love salsa! Today we're invited to join Chef Chris Maher and his wife Valerie Maher on a production day at Caleb and Milo. Caleb and Milo is an all natural salsa and spread company produced in Taos, NM. Located on the sustainibly focused Blackstone ...
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