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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Exploring Bonaire: Salt Flats, Donkeys, Diving & Dolphins!

Conor and Kelly welcome Conor's mother Charlie aboard Big Lost in Bonaire, exploring the island by truck and tackling a malfunctioning black water holding tank sensor.

Sep 30, 2025
Language: EN
Play Time: 00:29:12

Meet the Crew | Kelly – From Chaos to Calm: My Journey to Sea Life 💙⚓

Waiting on a catamaran survey in Fort Lauderdale, Kelly documents her transition from competitive equestrian arenas and high-stress real estate to full-time family ocean cruising.

Apr 22, 2025
Language: EN
Play Time: 00:11:24

Exploring Paradise: Shroud Cay Waterways, Warderick Wells & New Friends!

Sailing Big Lost navigates the mangrove creeks of Shroud Cay to swim the Washing Machine before sailing at 8 knots to Warderick Wells and hiking Boo Boo Hill.

Feb 11, 2025
Language: EN
Play Time: 00:19:04

Unlocking the Secrets of the Deep with PADI (Open Water Course)

Conor, Finn, and 10-year-old Maddie earn their PADI Open Water Diver certifications with Blue Water Divers in the British Virgin Islands, tackling regulator drills, CESA ascents, and reef dives off Norman Island.

Jul 13, 2024
Language: EN
Play Time: 00:24:06

Watch Sailing & Boating Adventures Around the World

Exploring Bonaire: Salt Flats, Donkeys, Diving & Dolphins!

Meet the Crew | Kelly – From Chaos to Calm: My Journey to Sea Life 💙⚓

Exploring Paradise: Shroud Cay Waterways, Warderick Wells & New Friends!

Unlocking the Secrets of the Deep with PADI (Open Water Course)

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