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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The Good Life: Cruising our Sailboat in the Bahamas (Calico Skies Sailing Ep. 17)
Calico Skies Sailing

The Good Life: Cruising our Sailboat in the Bahamas (Calico Skies Sailing Ep. 17)

After dreaming, scheming, and sailing for the past four months we are finally back in Bahamas and ready to settle into the cruiser life! It feels like the Bahamas were made just for boaters like us . . . perfect weather, zillions of islands to explore, secluded anchorages, and super clear water. In ...
Sailing to the Bahamas without a Gulf Stream crossing!! (Calico Skies Sailing Ep. 16)
Calico Skies Sailing

Sailing to the Bahamas without a Gulf Stream crossing!! (Calico Skies Sailing Ep. 16)

In previous episodes we provisioned and prepared our sailboat for a long blue water crossing, well my friends the time to embark has finally come! Join us as we sail 750 miles in 6 days from Puerto Rico to the Bahamas. We are treated to beautiful downwind sailing running north-west in the trade win...
Preparing our Sailboat for a Blue Water Passage to the Bahamas (Calico Skies Sailing Ep. 15)
Calico Skies Sailing

Preparing our Sailboat for a Blue Water Passage to the Bahamas (Calico Skies Sailing Ep. 15)

It's a busy few days in San Juan, Puerto Rico getting Calico Skies prepped and ready to go for our 750 mile sail to the Bahamas. We're planning for a seven day trip which means everything must be stowed away and the ship made ready for offshore blue water sailing. As per usual, we balance ...
Provisioning a Sailboat for the Bahamas Our Way! (Calico Skies Sailing Ep. 14)
Calico Skies Sailing

Provisioning a Sailboat for the Bahamas Our Way! (Calico Skies Sailing Ep. 14)

Many boats jumping to the Bahamas stock up in Florida. We are in the different position of heading to the Bahamas from the Caribbean, so we get creative and choose to do the majority of provisioning on the tiny island of Culebra! Or at least that was the goal.... -~-~~-~~~-~~-~- Thanks to our Patro...
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