Tradition Sailing Charters

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!

At first my husband and I discussed the expense of the trip, but after our day was said and done, it was will worth it! Thomas was our captain and did a great job commanding the sails! The rest of the crew was so much fun to converse with and enjoyed getting to know. We had a great group of people that took passage of her sails to Prickly Pear Caye. The snorkeling was the best of all the beaches we went to in Anguilla. We saw a sting ray, a manta ray, lots of vibrant fish, we fed the birds and ate an amazing lobster lunch! The fresh watermelon and chocolate Chip cookies were a godsend of food blessings on the journey back. We cannot express our gratitude enough for the whole crew! They collectively made our day of sailing, the best way to start of our new year of 2024!

My husband and I went on a sunset cruise with Tradition Sailing Charters. It was a punctual crew - and they were very friendly and fun! Our captain told us he is an Anguilla-native and was generous with his knowledge of the island.

We loved our experience with Tradition Sailing. It was the highlight of our trip. The Captain and crew were a joy to be with. The snorkeling was wonderful off Prickly Pear Island. The lobster was delicious. Great time, I would highly recommend this experience.

I cannot recommend the Sunset Cruise enough! It was such a special way to experience more of Anguilla. You truly felt like you were on a piece of history. The whole crew was so welcoming and fun to spend time with and they always made sure your cup was full! If you are on the fence just book it. You won't regret it!

Captain Thomas and crew were the kindest, most welcoming folks you could ever hope to spend an evening with. A first-class experience in every way. We’ll certainly be back on our next visit to the island.

Their half day sail and snorkel excursion was the highlight of my trip. The crew was professional and knowledgeable (about Anguilla and sailing!) and made it a very fun day. They took great care of us, kept our drinks full, served a delicious lobster roll lunch and took us to a good snorkel and lounge spot to spend our day. I highly recommend!

This exquisite sailing vessel is everything she is meant to be and more. With an outstanding crew whose expert sailing skills make it look easy, we enjoyed a day in Anguilla at Prickly Pear Pear beach that is unmatched. The crew was amazing, the food divine, and if you’re looking for a 5-star experience, this is it!

This was easily the best excursion my husband and I have both ever been on. Deb, Laurie, Thomas and Jasmine were all great hosts on the boat and made us feel right at home. We did the Prickly Pear sailing tour and the ride out there was amazing and the island was beautiful. We highly recommend.

This was a great evening. Thomas the first mate a young gentleman from Anguilla really made the trip. His local knowledge and love for sailing just topped off a really fun trip. We didn't see a sunset, because of clouds, Thomas pointed out star constellations, Venus and satellites moving through the Anguilla night sky. Great drinks and a very nice charcuterie spread all part of the Tradition made this sunset sail one to remember.

This is the trip that you want to book! The Lori and Deb were very attentive to all of the passengers needs and are just fantastic people, the food was awesome the beach was great and the crew and boat made it all better. If you are in Anguilla this should be on your bucket list as it is the experience of a lifetime. Lori, Deb and the crew bent over backwards for all of the passengers to make it a great tour. I lost my sunglasses on the ride from the sailboat to the dock to the parking lot, Lori found them and then brought them to my hotel. I just can't say enough about this trip.