Skip to primary navigation Skip to content Skip to footer

Anguilla Boat Charters

Sailing Cruises in the British West Indies

Incredible Cruises in Paradise

Sunset Sail Charters from Anguilla

Private Anguilla Sailboat Charters

Tradition Sailing in Anguilla


We’re excited to have the opportunity to share our passion of sailing on our beloved Classic West Indian sloop with you! Book one of our Anguilla boat charters and get ready for the experience of a lifetime.

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 sailing experience!


  • Most popular
From $420

This amazing sail to the Paradise island Prickly Pear is a day of indulgence that begins the moment your feet touch the deck of Tradition and only ends when we wave you goodbye. We’ll greet your with Morning Mimosas or a glass of freshly squeezed orange juice and feast on succulent grilled Caribbean lobster.


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.


Great fantastic day! Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

The crew did a great job taking care of all of us on the tour. I'd wouldn't hesitate going again! For anyone thinking about it, go ahead, it's well worth it.

– Tim O, TripAdvisor
Perfect evening! The Best Sunset Sail and Cocktail Hour in Anguilla

My husband and I took the sunset sail and it was wonderful!!! Thomas and Pepper were so fun and went out of their way to ensure our trip was memorable. Highly recommend this activity!!!!

– Kay C, TripAdvisor
Super Amazing! Half-Day Sail, Snorkel Adventure, and Lunch at Little Bay

This was one of the best parts of our vacation. The crew was so amazing and down to earth. We really had such an amazing time and will absolutely do this sail again when we come back!

– Cari, TripAdvisor
A must try! Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

The level of service was phenomenal. The crew was delightful and made sure our cups were never empty. They made sure we had everything we needed. The lobster lunch was amazing and Prickly Pear cay is so pretty and secluded.

– Dawn R, TripAdvisor