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.

Showing 1-7 of 7 results
Culebra BLEW our minds! day 5
Sail Stillwater

Culebra BLEW our minds! day 5

Welcome to the beautiful island of Culebra, Puerto Rico, where the crystal clear waters and pristine beaches create a serene haven for all who visit. Join us as we explore this stunning Caribbean gem, sailing across its azure waters and discovering its secluded spots. This 4K video captures the esse...
Sailing from St Croix to Culebra. USVI-SVI  Day 4
Sail Stillwater

Sailing from St Croix to Culebra. USVI-SVI Day 4

Day 4 of our Caribbean sailing adventure in the VIRGIN ISLANDS on a bareboat charter through the U.S. and Spanish Virgin Islands! Today we sail from St. Croix (USVI) to the island of Culebra, Puerto Rico, a favorite stop for cruisers and sailors traveling between the Virgin Islands and Puerto Ric...
The most underrated sailing itinerary in the Caribbean! The USVI and SVI
Sail Stillwater

The most underrated sailing itinerary in the Caribbean! The USVI and SVI

Join Brian and the crew as they sail a Bali catamaran through the USVI and SVI, taking on high seas, remote islands, and one of the most adventurous routes in the Caribbean. This isn’t your typical charter itinerary—it's rougher, wilder, and absolutely unforgettable. From offshore fishing (we ...
SAILING to One of the WORLD’S BEST BEACHES 🌴 EP-173
Leading the Escapade

SAILING to One of the WORLD’S BEST BEACHES 🌴 EP-173

Sailing the Spanish Virgin Islands to Puerto Rico, we fly our colourful gennaker, explore world-famous Playa Flamenco, and anchor at stunning Palomino Island. Subscribe for more sailing adventures, boat life tips, and off-the-beaten-path Caribbean gems! #Sailing #PuertoRico #BoatLife Sailing the ...
Our neighbors RUN AGROUND! – Sailing Vessel Delos Ep. 267
Sailing SV Delos

Our neighbors RUN AGROUND! – Sailing Vessel Delos Ep. 267

Have you ever wondered what the steps are for getting a catamaran off a reef? In this episode Brian helps our neighbors @tgt_sailing after they run aground negotiating a tricky harbor entrance. We also dig into some boat projects and fire up the new solar panels, and I cook up some super delicious...
The best way to explore is with a local- Culebra, Puerto Rico! – Sailing Vessel Delos Ep. 233
Sailing SV Delos

The best way to explore is with a local- Culebra, Puerto Rico! – Sailing Vessel Delos Ep. 233

*Limited Print* Long Sleeve SV Delos Sun Shirts featured in this video available now!- What’s the best way to explore a new island? We had barely dropped the hook at the small Puerto Rican island of Culebra before 2 locals approached us in their boat. It turns out they had been watching our vide...
Exploring Beautiful Culebra [EP 22] | Sailing Millennial Falcon | Sailing Around The World
Sailing Millennial Falcon

Exploring Beautiful Culebra [EP 22] | Sailing Millennial Falcon | Sailing Around The World

We leave Vieques and finally get the sails up as we head to the island of Culebra, the furthest island east of Puerto Rico. We explore the little vibrant town before starting our journey further east. Want more? Join us on Patreon! If your just joining us follow the journey from the beginning! ...
WeBoating
Logo
Shopping cart