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 25-37 of 37 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: -------...
Revival of Millenium: The BIG Splash ⛵️💦
Expedition Drenched

Revival of Millenium: The BIG Splash ⛵️💦

She’s Back in the Water! Our Epic Boat Splash After Months of Hard Work! 🚤💦 After 6 months and countless hours of dedication, sweat, and determination, the moment we’ve all been waiting for is finally here—our beloved vessel is back where she belongs: in the water! This milestone marks the end of a...
Overwhelmed and Defeated: Mistake Buying This Boat? 😫⛵️
Expedition Drenched

Overwhelmed and Defeated: Mistake Buying This Boat? 😫⛵️

We bought a new boat! Meet Millennium, our 23-meter steel expedition ketch, and join us on her first trip to the boatyard. From endless to-do lists to unexpected surprises, we’re feeling completely in over our heads as we tackle the realities of owning and restoring this incredible vessel. Watch as ...
I SPLASHED My Boat After A Year On The Hard
David Shih

I SPLASHED My Boat After A Year On The Hard

Get an exclusive @Surfshark deal! Enter promo code "DAVIDSHIH" for an extra 3 months free at When we arrived in Panama I was certain it would take 3 weeks to fix our boat....turned out I needed 44. But our boat is fixed and it's floating baby! Oh, and we have a celebrity fiberglasse...
I Surprised My Family With A Catamaran
David Shih

I Surprised My Family With A Catamaran

It's been almost a year since we bought the boat and I promised the kids a life on the water. Except I had to abandon them for a year to fix the boat. Today I finally get to show the kids their new boat for the 1st time! Then Carlos and I fiberglass the heck out of the entire middle bulkheads...
GOODBYE SAILING DOODLES
Taylor’s Travels

GOODBYE SAILING DOODLES

In this video I recap some great memories from Season 5 on @Sailing Doodles, before packing up my things to fly home. Thank you to everyone who made this season such a good one! This isn't goodbye forever :) To follow me on Instagram: @taylorfrancis_ Support me to continue making videos: Pa...
Catamaran Hatch Upgrade…Finally! Onboard Lifestyle ep.7
Onboard Lifestyle

Catamaran Hatch Upgrade…Finally! Onboard Lifestyle ep.7

This week on Onboard Lifestyle we remove sv basik's 25 year old hatches and make a serious upgrade to our Catamaran. Come back next week when we start a huge project...the salon windows! If you are interested in helping us produce these videos then please feel free to check out our Patreon pag...
Onboard Lifestyle ep.4 Guest Stateroom Done…Mic Drop!
Onboard Lifestyle

Onboard Lifestyle ep.4 Guest Stateroom Done…Mic Drop!

On this episode of Onboard Lifestyle we finish up a major project...our guest stateroom. Come back next week where we jump outside to start refinishing the decks. See you then! If you are interested in helping us produce these videos then please feel free to check out our Patreon page.
Onboard Lifestyle ep.2 Master head is nearly complete…the girls move in!
Onboard Lifestyle

Onboard Lifestyle ep.2 Master head is nearly complete…the girls move in!

On this episode of Onboard Lifestyle, Teal puts some finishing touches on our Master head and the girls get to move their stuff in. Check us out next week when we start a major project on SV basik...the guest stateroom. If you are interested in helping us produce these videos then please feel free...
Onboard Lifestyle ep.1 Building our Dream Catamaran
Onboard Lifestyle

Onboard Lifestyle ep.1 Building our Dream Catamaran

Join us this week as we tackle a big project on our custom 435 catamaran sv basik...a 100% refit of the master head. Come back next week where we complete this three month project. If you are interested in helping us produce these videos then please feel free to check out our Patreon page.
Mexico or Bust EP10, LaterThanWeThink, SV Angelique of Vancouver
Later Than We Think

Mexico or Bust EP10, LaterThanWeThink, SV Angelique of Vancouver

SV Angelique of Vancouver Mike and Jacquie make the big announcement about their future sailing plans.... want a hint.... We are heading south till the butter melts Music used in this Video Opening and Ending Credits Rotten Gardenias - HUMA HUMA Other Music One Fine Day Find Us At: YouTube - Fac...
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