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“sunset cruise”(18 reviews)
“sandy ground”(20 reviews)
“lobster”(10 reviews)
Adventures on a Classic West Indian Sloop. Tropical Cay Lobster Lunch Cruises, Sunset Cruises, Exclusive Private Escapes.Sightseeing. Enjoy luxury and indulgence on our rustic and historical trading sloop.
| Sandy Ground, The Valley AI-2640, Anguilla
+1 264-476-7245
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Ways to Experience Tradition Sailing Charters
from $230.00
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Reviews (121)
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All reviews sunset cruise sandy ground lobster prickly pear island homemade chocolate chip cookies snorkeling trip rum punch beautiful boat old friends great hosts made us feel at home piece of history special experience an amazing experience wonderful lunch wonderful excursion explore the island
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1 - 10 of 119 reviews
Reviewed 4 days ago

It was wonderful! I recommend it highly. The crew- owners plus 1- were very knowledgeable and had great command of the boat. Beverages and food were great also. A highlight of our trip!

Date of experience: February 2019
1  Thank Curiosity539776
Reviewed 5 days ago

We were scheduled to do the prickly pear tour but the wind made it so that the restaurant on the island could not operate. Instead, we altered course and went to Little Bay, Crocus Bay and then sailed West along the coast. While I was...More

Date of experience: February 2019
1  Thank maackel
Reviewed 6 days ago

My wife and I joined Laurie, Deb, and mate for their sunset cruise on 15 February. There were 3 other couples--all unrelated. By the time we returned to Sandy Ground two hours later, we felt like we had met new and interesting friends. The highlight...More

Date of experience: February 2019
1  Thank flakcatcher2001
Reviewed 6 days ago

We enjoyed this very much. It was interesting, the lobster lunch was very good, Deb and Laurie were wonderful hosts as well.

Date of experience: February 2019
1  Thank AKDeup
Reviewed 1 week ago

This was my wife and I's favorite activity during our time in Anguilla. Amazing sloop, awesome hosts, great food and drink and snorkeling out on Prickly Pear. If you're in Anguilla, you can't miss this activity!

Date of experience: February 2019
1  Thank Mark H
Reviewed 1 week ago

We had such an amazing time on our sunset sail with Capt. Laurie, Deb, and Thomas. They were very gracious hosts, and Tradition is a lovely sailing vessel. The sunset was spectacular that evening, and we were treated to the famous "green flash." This is...More

Date of experience: February 2019
1  Thank Kathy B
Reviewed January 18, 2019

We loved everything about this sunset cruise. The boat itself is a piece of history and crew of three works together as one. They clearly know their sailing and are incredibly friendly. Great food and drinks and the views from the water are simply spectacular....More

Date of experience: January 2019
2  Thank BarbKnowles
Reviewed January 14, 2019

Laurie and Deb were great hosts. Flexible on what we wanted to do and the lunch was superb and they had a great selection of drinks. The boat is a real treat with all the original character.

Date of experience: January 2019
2  Thank LAC69
Reviewed December 31, 2018

This was the third time my family has sailed on The Tradition; our first to Prickly Pear for lunch, though. The trip was excellent. The boat is a classic, and beautiful, old cargo sailing vessel that has been meticulously restored by its owners. And there...More

Date of experience: December 2018
1  Thank DTW2AXA
Reviewed December 29, 2018

Deb and Lori took us out for the 4 hour tour. The best think we did while on Anguilla!! They are fantastic hosts! The boat, tour, food(!!) and drinks provided for a fantastic day!

Date of experience: December 2018
2  Thank Bob M
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Questions & Answers
Ask a question
Kristy C
September 14, 2018|
AnswerShow all 4 answers
Response from Deborah V | Property representative |
Hi There! So sorry for not seeing this earlier. Our first sail is November 7th! Hopefully we get the opportunity to take you sailing. Cheers, Deb
deborah b
June 27, 2015|
AnswerShow all 2 answers
Response from Deborah V | Property representative |
Hi Deborah! Thanks for your interest in Tradition Sailing Charters and our Classic West Indian Sloop. Our prices vary depending on the type of sailing adventure you're looking for. For a comprehensive list and... More
Travel Forum Posts
Boston, Massachusetts
Which one? Tradition Sailing Charters vs. Chocolat (2 Replies)
Hello Anguilla Forum! Traveling in April for the first time ever and we can't decide between the Tradition Sailing Charter or the Chocolat Boat trip. Could we have your suggestions, input...etc.? One preference over the other? Thank you everyone!
February 17, 2014|
Response fromaxa_beachlver|
I have sailed on Chocolat about 20 or so times and it's always the highlight of my trip. You will go to Prickly Pear and Sandy Island. Lunch on PP is always good, your choice of ckn, ribs or fish. Plenty of drinks on board...snorkeling equipment is provided if you don't have your own. Twelve people maximum, which makes it nice. Capt. Rollins and Deon will take good care of you, and they are a lot of fun...for only 80.00 per person for a full day, I think its one of the best deals around. I...More
Las Vegas, Nevada
Tradition Saliling Charters is ready to go! (4 Replies)
Both trips sound really great - I would love to do the Sunset Cruise: From FacebookL We would like to announce that Tradition Sailing Charters is ready for Season 2 and ready to take your reservations. We continue to offer Tropical Cay Lobster Lunch cruises on our Classic West Indian Sloop, and as always are committed to providing an extraordinary experience and exquisite service. Tropical Cay Lobster Lunch Cruise includes: A full day of sailing on Tradition Morning Mimosa’s or...More
January 22, 2014|
Response frombeachfan101|
Thanks for sharing this Ellen. It DOES look amazing. This may just be enough to make get out of that lounge chair and have this adventure.