Traditional Sailing Adventure to Anguilla's Prickly Pear Cays: An Authentic Caribbean Experience

Embark on a traditional sailing adventure to Anguilla’s Prickly Pear Cays. Immerse yourself in stunning reef snorkeling, enjoy a Caribbean barbecue on the beach, and sip on Pina coladas at the tiki beach bar. Limited spots available!

Duration: 6 hours
Cancellation: 24 hours
Highlights
  • Tradition Sailing Charters - Step onboard the last surviving Caribbean sloop of her kind and indulge in an authentic and unforgettable sailing experience. Join Tradition for a magnificent sail to a tropical paradise where a beachcomber’s paradise awaits. It’s a day of indulgence that begins the moment your feet touch the deck and only ends when we…
What's Included
  • Local guide
  • Unlimited drinks (open bar)
  • Lunch
  • Goods and Services Tax (GST)
  • Authentic Sailing on a Historic Caribbean Sailing Vessel
  • Use of snorkel equipment & swim aids
What's Not Included
  • Gratuities
  • Hotel pickup and drop-off
Additional Information

Constructed in 1978, Tradition was initially used for sail commerce across the Caribbean. It has since transitioned from trading goods and smuggling contraband to hosting charter guests for leisure cruises around Anguilla. This authentic sailing experience is a vital addition to your visit to Anguilla. Experience the simple elegance of rustic sailing as…

Location
6W25+9R Sandy Ground
Departure Point: Sandy Ground Dinghy Dock We will pick you up at the Sandy Ground Dinghy Dock at the time of your departure.   Dates: See Availability
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(86 Ratings)
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216kareym
Jun 29, 2025
Great sailing excursion! - 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.
Review provided by Tripadvisor
Floydfreedom
Apr 1, 2025
Another Great Sail to Prickly Pear - This is a fantastic day sail to Prickly Pear and back. The hosts are a delight and a vast reservoir of local history. The service is grand. Once on Prickly Pear you can snorkel around; keep moving and you'll run in to some good sightings of fish, rays, turtles, etc. Lunch was delicious. Be careful with the drinks. It's easy to get hammered early in the long day of sailing and then the captain and his crew are forced to babysit you; it's not good for anyone.
Review provided by Tripadvisor
Howard
Mar 28, 2025
Great ride and amazing food and service - We had a great sail. Staff and service was first rate. So friendly did not want to leave. Lots of drinks and great food. Thanks guys for a memorable day.
Review provided by Tripadvisor
Dar0sey
Feb 28, 2025
Perfect day on the water - Our favorite day on the island! Not to be missed! Laurie & Deb are fabulous hosts, and the sail was enjoyable from beginning to end. Prickly Pear is beautiful, and definitely worth the time and cost.
Review provided by Tripadvisor
Ca_nyc_traveler
Feb 7, 2025
A true trip highlight - Fantastic sailing day and a highlight of our group trip to Anguilla. Deb, Laurie and Maria were just fantastic and made sure we were so well taken care of throughout the day. Lunch was delicious and relaxation time on Prickly Pear was great fun. Highly recommend a private charter on this stunning wood sailboat with so much great history behind her.
Review provided by Tripadvisor
Etiennette_clamouze
Dec 13, 2024
A MUST DO - Deb, Laurie and their crew are the BEST! Laurie sharing his knowledge and the most amazing stories during the trip is an absolute delight! Once arrived on Prickly Pear, they transformed into your own personal butlers, you have nothing else to do than relax, enjoy the delicious food and drinks! I want to go again! it is a MUST DO in Anguilla. Sweet touch at the end with the delicious homemade cookies to go!
Review provided by Tripadvisor
Kenneth_v
Jun 7, 2024
What a great day on the water ! - This trip was a blast , captain and staff were the best . They made sure everybody was taken care off with drinks , food , etc.
Review provided by Viator
Caitlinmoyna
May 20, 2024
Just book it - NOW!! - After reading the reviews, we decided to book the Tradition trip to Prickly Pear, and boy it did not disappoint! It started before the trip when Captain Laurie and Deb spoke with me about my concerns regarding my husband's broken foot and how he would get on and off the boat. They assured me all would be ok, and indeed, they made every effort to accommodate him. So glad he did come along because he agrees it was our best day on Anguilla. We were treated to a history lesson first, then a lovely sail out to Prickly Pear, followed by snorkeling among thousands of colorful fish, and the most amazing lobster meal on the beach. After that, we enjoyed chatting with the group as Deb poured us many adult beverages, delivering them right to us in the water. The day was capped off with a perfect sail back to Sandy Ground, warm chocolate chip cookies, and more beverages. All the guests got along so well with each other, which was largely a testament to how comfortable Laurie and Deb made us feel. The entire Tradition crew worked tirelessly all day long to ensure we would have an incredible experience - which is exactly what we did!! Can't say enough great things about this adventure - just go ahead and book it so you see for yourself!
Review provided by Tripadvisor
Mary
May 10, 2024
Definitely worth the wait! - Our Saturday sail was cancelled due to weather but fortunately they were able to reschedule for Sunday. The weather was perfect, the crew was attentive, the meal was delicious and the sailing was delightful. Captain Laurie, Deb and Bea kept us entertained all day long. So many great things about this adventure but you need to experience it for yourself. Definitely the highlight of our week in Anguilla.
Review provided by Tripadvisor
Jordanas1000
May 8, 2024
Perfect sailing day - Third time to Anguilla and third Tradition trip. The day sail to Prickly Pear was perfect in every way — the crew is phenomenal and attentive, the time on sea and land is perfect. Do not hesitate to book with Laurie and Deb. Top-notch, high-end experience.
Review provided by Tripadvisor
From $644
up to 12 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).