Sailing
2–3 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 100% of travelers
100% of reviewers gave this product a bubble rating of 4 or higher.
from
$368
per adult
Tradition Sailing Charters
Tradition Sailing Charters
5
Full view
About
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.
Tours and Tickets by Tradition Sailing Charters
Sailing
6 hours
Free cancellation
Not sure? You can cancel this reservation up to 24 hours in advance for a full refund.
Recommended by 100% of travelers
100% of reviewers gave this product a bubble rating of 4 or higher.
from
$644
per adult
Travelers talk about
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Most Recent: Reviews ordered by most recent publish date in descending order.
Detailed Reviews: Reviews ordered by recency and descriptiveness of user-identified themes such as wait time, length of visit, general tips, and location information.
Popular mentions
5.0
282 reviews
Excellent
280
Very good
1
Average
0
Poor
0
Terrible
1
Jonathan R
Indian Harbour Beach, FL16 contributions
Apr 2021 • Friends
If you are looking for the best sailing experience or just want to enjoy the beautiful water and scenery of Anguilla look no further, Tradition Sailing Charters offers the first class experience you are searching for. The hospitality, hordeurves, cocktails, smiles and laughs keep going during your whole journey with Laurie and Deb. There is something very special about this beautiful hand crafted 1978 schooner that will capture your heart and is an unforgettable experience!
Written April 11, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
DavidVa999
Herndon, Virginia74 contributions
Feb 2020
My wife and I went on the sunset sail and highly recommend it to everyone. The boat is beautiful, the crew is extremely friendly and the whole experience is fantastic. When we got to the boat we were greeted on the boat by Deb with a passion fruit/rum/sparkling wine drink. We left at 4:30 from Sandy Ground and sailed along the coast toward Little Bay. The sunset was amazing and then there were clear skies and you could see millions of stars. We got back at 7:30, so we had 3 hours on the boat, which was perfect.
Written March 12, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Mark
2 contributions
Feb 2020 • Solo
I’ve taken multiple trips on Tradition. The experience never gets old only better each time. Captain Laurie and his crew immediately set a relaxed and welcoming tone as well as bottomless mimosas if you want and then any other beverage of your choice throughout the trip. Tradition is a sturdy and stable vessel making for a comfortable ride. While the price may at first seem like a lot it is worth every penny.
Written February 3, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thanks Mark! Your feedback means so much!
Written February 5, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Brittany B
The Valley, Anguilla18 contributions
Feb 2023 • Couples
We did the sunset cruise with Deb and her team and it was a nice experience overall! The boat is gorgeous and the staff gives you some history on the boat which is a nice touch. The champagne and snacks provided were amazing. The only reason I’m giving 4 stars is because I felt it was overpriced at over $500/couple and you had to take a little dingy boat to the sailboat and it was not easy to get in/out and was challenging if older.
Written February 18, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
dicap2018
Philadelphia, PA9 contributions
Jan 2020
magical day on the water. full day sail with top notch service. From our first email to Deb to the days after the sail she went above and beyond to make our stay in anguilla everything we hoped for. Lauri, Deb, Thomas, and Hanna provided us with a day we will always remember, a private sail out to a deserted island with a gourmet lunch. cocktails were freely flowing all day and cold water seemed to appear in your hand just when you needed it! this is a must do!
Written January 22, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you! We really appreciated being part of your anniversary adventure. We look forward to the next time!
Written February 5, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Buffy F
1 contribution
Dec 2023 • Family
We sailed on the full day prickly pear
Snorkel and lunch tour with two teens (14 year old girls). 3/4 of the guests were repeat customers! The trip was amazing and there was something for everyone. The owners and staff were incredibly accommodation. Our daughter’s friend is not a seafood fan and when she didn’t like the lobster (it was delicious!) they were quick to bring her chicken and ribs instead. The mimosas, cookies and rum punch were wonderful. They even let my daughter and her friend steer the boat on the way back! Don’t be thrown off by the price. The trip is very, very well worth it. We already can’t wait to come back again.
Snorkel and lunch tour with two teens (14 year old girls). 3/4 of the guests were repeat customers! The trip was amazing and there was something for everyone. The owners and staff were incredibly accommodation. Our daughter’s friend is not a seafood fan and when she didn’t like the lobster (it was delicious!) they were quick to bring her chicken and ribs instead. The mimosas, cookies and rum punch were wonderful. They even let my daughter and her friend steer the boat on the way back! Don’t be thrown off by the price. The trip is very, very well worth it. We already can’t wait to come back again.
Written December 26, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
I'm thrilled to hear that your full day Prickly Pear snorkel and lunch tour was a hit, especially with the teens! It's always rewarding to know that our guests, including the many repeat customers, find something special in each trip. It's great that your daughter and her friend got a chance to steer the boat, adding to the adventure. We're proud that the experience felt worth the price for you, and we can't wait to welcome you back for more memorable trips! Thank you for sharing your wonderful experience with us.
Written January 14, 2024
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Natalie H
1 contribution
Feb 2023 • Couples
The lobster lunch sail was a highlight of our trip for sure! The Tradition Sailing team is top notch and we had a wonderful experience from start to finish. The crew was so friendly, knowledgeable and attentive to every need! Prickly Pear was stunning and the lunch the crew served there was fantastic. This tour is a must do in Anguilla!
Written February 19, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
RL Hughes
8 contributions
Mar 2020
One of the absolute highlights of our trip. Wonderful stories, amazing conversation and company, just loved every moment. Could not recommend higher! Love the special drinks and yummy cheese and wow bacon wrapped figs Oh MY! just a spread! Laurie and Deb just consummate hosts.
Written March 6, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Steve Wilhite
3 contributions
Jan 2020
Loved spending the New Year’s Day (Tradition team first trip of 2020) with Laurie, Deb, Thomas and Hannah sailing out to Prickly Pear. Loved hearing their individual and collective stories. Had a rainy ride out, but they made it great. Service was excellent and had a ton of fun with them. Beautiful weather and ride back with some great people.
Written January 3, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
LA H
Indianapolis, IN352 contributions
Feb 2020 • Couples
We spent the best day sailing with Tradition. Laurie, Deb, Thomas, and Hannah are excellent hosts! The Tradition sailboat was a beautiful, comfortable vessel. Deb served the best lobster rolls, Greek salads, chocolate chip cookies all made from scratch. Little Bay was beautiful! In addition to the wonderful snorkeling, the bird sighting was excellent. Drinks and good conversation among crew and guests flowed freely. It was a most memorable day and definitely a must do when in Anguilla.
Written February 18, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Thank you! Your review means a lot to the entire crew!
Written February 24, 2020
This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
Hi There! Thank you for your question, and apologies over the late reply.
We do recommend that children join us on our day excursions. Our minimum age for shared excursions is 4 years old. Our private excursions do not have an age limit as the entire group is committed to ensuring our young sailors are having a good time, and we can adjust our excursion to suit the needs of the child.
We always pay special attention to our young sailors and ensure they are safe and comfortable during our excursions.
Thanks again!
Deb
Written May 13, 2019
What months does Tradition operate? We will be visiting late November.
Written September 14, 2018
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
Written November 2, 2018
we are staying from january 23 - feb 1 how much is your sunset cruise ? what time does it leave and return? what is included?
Written January 11, 2016
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 description of each of our excursions, I recommend checking out our website - although I'm unable to post a link from here.
Or, if you send me an email I can send you information on all of our current packages. I would attach here, but I don't think it's possible.
Thanks again!
Deborah
Tradition Sailing Charters
1-264-476-7245
Written July 1, 2015
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