Tradition Sailing Charters Anguilla
Boat tour agency · Blowing Point ·

Tradition Sailing Charters Anguilla

Boat tour agency · Blowing Point ·

Sailboat charters offering sunset cruises, snorkeling, and history

Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by Photo courtesy of Anguilla Tourist Board
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null
Tradition Sailing Charters Anguilla by null

Information

5218 Sandy Ground, Sandy Ground 2640, Anguilla Get directions

Information

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5218 Sandy Ground, Sandy Ground 2640, Anguilla Get directions

+1 264 476 7245
tradition-sailing.com
@traditionsailinganguilla
𝕏
@sailtradition

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Last updated

Dec 2, 2025

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20 Best Things to Do in Anguilla, According to Experts

"A classic West Indian sloop experience ideal for a sunset cruise along the coastline, where guests can relax with well-made cocktails and Caribbean bites while taking in sweeping coastal views." - Carley Rojas Avila Carley Rojas Avila Carley Rojas Avila is a bilingual travel writer, editor, and content marketer. She is an expert on Latin America, the Caribbean, and Cuba, as she lived and worked in four different countries in that region. Carley founded the digital travel publications Loosely Local and Home to Havana. Travel + Leisure Editorial Guidelines

https://www.travelandleisure.com/best-things-to-do-anguilla-7568188
Tradition Sailing Charters Anguilla
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25,132 Postcards · 3,700 Cities

"Explore Anguilla by Sailboat Sailing is Anguilla’s national sport, but it’s also the best way to explore the island's dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here."

The Best Things to Do in Anguilla
Photo courtesy of Anguilla Tourist Board
Tradition Sailing Charters

Brett L.

Google
We had a spectacular time on the full day excursion to Prickly Pear island. We were on the last trip of the season before they sail down to Carriacou for yearly maintenance during hurricane season. Dylan, Thomas, and Deb were very knowledgeable about the history of the island and the boat. The rum punch was strong and watermelon fresh. Could not have asked for a better time!

Raymona P.

Google
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.

Shannon S.

Google
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!

Jason M.

Google
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.

anguillagrl

Google
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!!

Kristin H.

Google
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!

Kevin V.

Google
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.

Lennie t

Google
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!