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TJOS Sailing

Welcome to The Joy of Sailing Carib!

The Joy of SailingSM Friends and Family are invited to join us in the Caribbean! Escape the cold winter months and enjoy gorgeous sailing adventures in warm waters.

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A Sailing Experience Like No Other

We sail together in the summer, let's expand our horizons and enjoy the glorious warmth of the Caribbean islands.

We primarily visit the islands between Grenada and Martinique picking up and returning crew to the same island for easy travel.  Are you friends or family (F&F) or interested in Women Only Sailing? If yes, check out our Crew Opportunities and the Winter 2026 sailing schedule then reach out to set up your winter adventure!

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Adventurers & Explorers

Share your amazing experience with The Joy of Sailing Carib. We'd love to hear your stories and feedback.

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Sailors' Corner

Explore our blog for captivating sailing stories, travel tips, and the latest news from The Joy of Sailing Carib.

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