About Tradition Sailing Charters – Anguilla’s #1 Sailing Adventure

Rated by TripAdvisor as Anguilla’s #1 Sailing Adventure, Tradition Sailing Charters offers an authentic Caribbean sailing experience

Tradition was hand-crafted, in 1978, on the beach in Carriacou, Grenada. Built for sail trading through the Caribbean, she worked the trade winds, carrying cargo – including contraband from St. Barthelemy where the smuggling trade in alcohol and cigarettes thrived until as recently as the 1990’s.

Instead of island trading, Tradition is now living in semi-retirement in Anguilla and now sails to capture the romance of a Caribbean past. 

She will also capture your heart. 

As you feel the wooden deck beneath your feet, you are instantly connected to West Indian maritime days of old. You think of the past, of the men who built her, who worked on her, who loved her.

We’re excited to have the opportunity to share our passion of sailing on our beloved Classic West Indian sloop with you!

If you’re a hard-core sailor, a fair weather boater, or even if you’ve never set foot on a sailboat before, we’re here to provide an unforgettable Anguilla experience!

Fair Winds!

Laurie & Deb

The wonders of the sea are as marvelous as the glories of the Heavens

– Matthew Fontaine Maury

Luxury and Adventure.

Book online or call +1.264.476.7245 to reserve your amazing tropical experience.