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Tradition Sailing in Anguilla

A message to our guests and friends ⛵

As many of you know, every September and October we take Tradition out of service for her annual maintenance, and we’d planned to welcome you back aboard on November 23rd.

This year, as we looked at the work ahead, it became clear she needs more than her usual seasonal care. She’s scheduled for an extensive refit, and we know it will take some time to do properly.

After a lot of thought, we’ve made the difficult decision not to reopen on November 23rd and to take the coming season off. We know many of you had already booked with us, and we’re truly sorry for the disappointment this causes. This time will let us complete her refit without rushing, and to reboot and reevaluate how we can best serve you in the years ahead.

Important Booking Information

🔹 Online bookings are closed for the season.
🔹 All existing bookings and gift cards will be refunded automatically to your original payment method within 7 business days. There’s nothing you need to do.

Taking the year was not an easy decision. Many of you have sailed with us for years, and some of you were looking forward to your first trip. Thank you for your understanding, your patience, and all the support you’ve shown us. We can’t wait to welcome you aboard again. 💙

Follow along here and on Instagram for updates on her refit.

With gratitude,
Deb and Laurie

#TraditionSailingAnguilla #Anguilla #Sailing

ANGUILLA PARADISE SAILING CRUISES

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!

POPULAR SAILING PACKAGES

MORE ABOUT TRADITION SAILING

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.

WHAT OUR CUSTOMERS THINK OF US!

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

THE TRADITION VIDEO