Tradition Sailing Charters Anguilla

Took the Tradition's Sunset Sail on Friday, May 9. What a perfect way to end our Anguilla trip. Captain Laurie, Deb and Marie were amazing as always. The perfect hosts - making sure your glass was never empty and the food was delicious. The sail was so smooth and finally got to see Little Bay (next trip will be their half day sail). The clouds marred the sunset slightly but it was still gorgeous and the most perfect ending - dolphins escorted back toward Sandy Ground. Just magical. I cannot recommend Tradition Sailing Charters enough. The history of the boat is fascinating and the crew are phenomenal.

We took the half-day snorkel sail to Little Bay, and it was amazing. The boat glides like a dream, and best of all, there is no loud engine noise and the smell of gas on your trip. Little Bay is beautiful with calm waters to swim in, and a really nice rock wall with lots of birds, cactus and nice snorkeling under the rock overhang. Laurie, Pam and crew are very attentive and have great stories about the history of the boat and the islands. Highly recommend!

What a fantastic day out under sail on the waters heading to Prickly Pear Cay for some delicious lobster lunch! Captain Laurie is extremely knowledgeable about the island and sailing having grown up here. His crew were so friendly and nice, we all felt like family. The snorkeling was perfect. Many thanks to everyone making our trip unforgettable!

A trip to Anguilla is not complete without an evening sail on Tradition! We have enjoyed this evening sail at least a half dozen times. Captain Laurie, Deb, and their mates are top notch. Their knowledge, service, and friendliness are superb. The hors d'oeuvres are well thought out and tasty. Oh, and all refreshments are included as well! Treat yourself!

This sailing excursion was a blast and we had so much fun! The sail (both to and from Prickly Pear Cays) was a ton of fun and Deb made sure we had plenty to drink and snack on! The crew were all very friendly and took great care of all the passengers. Snorkeling off of Prickly Pear Cays was amazing - tons to see in the reefs! The lunch was very tasty - everyone in our party had the lobster plate.

There are not enough superlatives to describe a sunset cruise on Tradition. The boat-a real beauty: solid, beautifully maintained and a testament to boat building in the Caribbean. The crew-professional but fun, they work hard to make your trip memorable & pleasant. The scenery-seeing Anguilla from the water is a unique experience that everyone should have at least once! The raw beauty is breathtaking-Dover style cliffs, wild beaches & wonderful sea life including sea turtles, dolphins, pelicans & goats! All of this while sipping fabulous cocktails and having tasty nibbles with your new found on board friends. Truly a must do when visiting Anguilla. Thanks to Captain Thomas, First Mate Deb and Dylan for a fantastic evening!!

Wonderful experience! This was my first time visiting Anguilla and sailing. The crew (Lori, Deborah, and Thomas) were exceptional. They were informative, had funny quips, and were able to hold conversations with all the guests on the boat. Lunch was also delicious. They gave us more than enough time to snorkel and play in the water. Would recommend to anyone looking for a memorable experience.

Five-Star Experience – Truly Exceptional! This was truly a five-star experience—the service, the crew, everything was absolutely on point! I loved how the ship has a story and history behind it, and the crew members were so friendly and open, sharing their own stories too. The drinks, the service, the safety—every aspect was top-notch! One standout highlight was the stop at Prickly Pear for lunch. The incredible service didn’t stop on the boat—they set up our beach chairs, brought us drinks, took us to lunch, served us, and brought us back to the boat. It was seamless and so thoughtful! I’ve done charters around Anguilla, St. Martin, and St. Barts, and while I’ve loved them all, this one is my favorite. (Sorry, other favorites—but this was the best service by far! 😄) Thank you for an amazing day out—can’t wait to do it again!