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Happy Island Charters boat charters and boat trips in the US Virgin Islands, St Thomas and St John

The #1 Virgin Islands Sailing Yacht Experience 

Why Book With Us?

Snorkel with
Sea Turtles!

Happy Island Charters Boat Charter St Thomas US Virgin Islands

Sail on a Classic Yacht!

Pedro the Pirate Dog sailing with Happy Island Charters in the US Virgin Islands

Hang with Pedro!

Eat, Drink and Relax!

This is Sailing at its Finest!

Choose your Adventure


Full Day Charter

Experience the ultimate in luxury day charters with our flagship full day private charter. Sail, snorkel, and relax aboard our classic yacht, enjoy our premium open bar and our famous 'Lowcountry Boil' with Caribbean lobster. Book now and let us show you the best of the Virgin Islands!


Half Day Sail

Sail the crystal clear waters of the US Virgin Islands on our private half-day charter! Swim, snorkel, and enjoy our open bar with delicious hors d'oeuvres, or head to Pizza Pi VI for lunch on this family-friendly adventure.


Sunset Sail

Watch the sun dip below the horizon and the sky light up in a spectacular display of colors with our private sunset sail charter. Sip on chilled sparkling wine and indulge in a delicious selection of hors d'oeuvres while taking in the stunning views of the Virgin Islands from our classic sailing yacht.

Happy Island Charters sailing in the US Virgin Islands
Pedro the Pirate Dog

Book Your Charter Today

Cannonball! Have a ball on a boat trip with Happy Island Charters in the US Virgin Islands

What People Say About Us 

"Our family had a fantastic time with Happy Island Charters!! Fancy, Jodie, and Pedro were the absolute best- friendly, hospitable, and informative! The food and drinks were amazing and never stopped coming. The snorkeling and water activities were a blast as well! 10/10 recommend- we cant wait to go back"

Jenny Holloway

Follow Us @happyislandcharters

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