Watch Sailing & Boating Adventures 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.

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Good Times with Friends in the Caribbean – S4EP8
Taylor’s Travels

Good Times with Friends in the Caribbean – S4EP8

Get 10% off your first month of therapy with my sponsor BetterHelp: In this episode we leave Canouan and sail back south to Union island to meet up with our good friends @OddLifeCrafting and enjoy a ton of waters ports together! Thanks for watching! Be sure to give the video a thumbs up and SUBSC...
Waterfalls, Ziplines & Motorcycles – Dominican Republic 🇩🇴 – S3EP14
Taylor’s Travels

Waterfalls, Ziplines & Motorcycles – Dominican Republic 🇩🇴 – S3EP14

This episode is packed full of adventure! We have a bit of a sketchy incident upon our late night arrival and woke up the most rolly anchorage ever. We move into Luperon and set out on a grand adventure for Aj and Nelly's last few days. We rent motorcycles and ride over to a well known spot in ...
Our Longest Passage Yet! Sailing to Dominican Republic – S3EP13
Taylor’s Travels

Our Longest Passage Yet! Sailing to Dominican Republic – S3EP13

In this episode we set sail from Turks and Caicos to Dominican Republic, our longest passage on Gypsy Moon yet! Although we had to change course to a different destination we had a great sail an arrived in DR around 2:00am. If you enjoy my videos please like and/or comment! Also don’t forget to SU...
Leaving My Monohull For A CATAMARAN?!?! – S3EP3
Taylor’s Travels

Leaving My Monohull For A CATAMARAN?!?! – S3EP3

In this episode I take a short break from working on my boat to join Tara and friends on a charter in Key West with Restless Native Charters. It was a wonderful break from the reality of the to do list still ahead of me. But after some fun I return back to work and get a ton of projects completed. ...
Refitting My 38ft Sailboat – S3EP2
Taylor’s Travels

Refitting My 38ft Sailboat – S3EP2

Click my link to try AG1 by Athletic Greens - Get 1 Year supply of Vitamin D3K2 & 5 FREE travel packs: Time to check some things off the to do list! In this episode I get some help from Ryan and Kiki to get some big jobs done. We install my new solar arch, radar and anemometer. Thanks for wat...
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