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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Crossing the Pacific Changed Our Family
Aboard Sailing Big Lost, Connor and Kelly complete a 24-day Pacific crossing from Panama, arriving at Nuku Hiva in the Marquesas after 4,000 nautical miles.
We Left the Boat | Visas, Passports & Panama City
Kelly and Connor leave their catamaran at Shelter Bay Marina to tackle long-stay visa applications, U.S. Embassy passport renewals, and family visits across Panama City before setting sail for San Blas.
From Sea to Streets: Sailing into Cartagena & Touring the Walled City
Sailing into Cartagena Colombia, Sailing Big Lost crosses 400 nautical miles from Bonaire, dodges Magdalena River logs, clears a harbor net, and explores the historic Walled City.
Bonaire to Cartagena! Our Caribbean Passage
Sailing Big Lost departs Bonaire on a 420-nautical-mile passage to Cartagena, Colombia. The crew replaces a leaking raw water pump underway, navigates nocturnal lightning storms, and hoists their Code 55 gennaker sail.
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.
Into the Wind: Sailing East to Sint Maarten
Sailing Big Lost navigates an upwind passage from Virgin Gorda to Sint Maarten aboard their Vision 444 catamaran, clearing sargassum from the propellers and installing upgraded alternators in Simpson Bay.
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.
Survey Day – Will BIG LOST Pass the TEST?
Connor and Kelly prepare Big Lost for a prospective buyer survey in Freeport, Bahamas, navigating haulout delays, drive shaft strap clearances at Bradford Marine, and rigorous hull inspections.
Sailing Into the Future: What’s Next for Big Lost?
Cruising the Exumas aboard catamaran Big Lost, Connor and Kelly complete transmission repairs at Staniel Cay, ride out gale winds, and make the big decision to sell their Leopard 62.