Traditional Sailing Adventure to Anguilla's Prickly Pear Cays
Overview
Available languages
6 hours
Mobile ticket
Built in 1978, for sail-trading throughout the Caribbean, Tradition has exchanged sailing cargo and contraband for cruising with charter guests and cocktails in Anguilla. This authentic and traditional sailing experience is a must do on your Anguilla itinerary. Sail in rustic luxury, while sipping Mimosas or hand-squeezed orange juice, to one of the jewels in Anguilla’s Marine Park System, the Prickly Pear Cays. Immerse yourself in the stunning reef snorkelling, a delicious Caribbean barbecue on the beach, and Pina coladas at the tiki beach bar. Enjoy the white sand beaches, explore the nesting grounds of sea birds, and hand-feed the bananaquit birds before re-boarding Tradition around 1:30 pm. It's an adventurous and exhilarating upwind sail back to Road Bay and Sandy Ground, a day made complete with rum punch, Tradition's chocolate chip cookies and fresh watermelon. Tradition hosts a maximum of 12 guests and space is limited to a maximum of 12 guests on this 6 hour sail.
Additional Info
Suitable for all physical fitness levels
Minimum numbers apply. There is a possibility of cancellation after confirmation if there are not enough passengers (6) to meet requirements. In the event of this occurring, you will be offered an alternative or full refund
Please advise any specific dietary requirements at time of booking
Not recommended for travelers with serious shellfish or nut allergies
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
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 wave you goodbye. Once you're served Morning Mimosas or freshly squeezed orange juice, the Captain will conduct a short safety briefing and some history of Tradition's life as a Caribbean sail-trader and rum smuggler. Help us raise the sails or simply relax and watch for turtles, flying fish, dolphins and during their migration, even whales. We'll also throw out a fishing line and see if it's our lucky day. We'll depart Prickly Pear by 2 to begin our sail back. We'll keep you refreshed with rum punch, chilled wine, or beer and make sure your sweet tooth is satisfied with Tradition's signature homemade chocolate chip cookies and freshly sliced watermelon.
Prickly Pear Cays
Snorkel the Prickly Pear reef. Swim and float along the shore. Search for shells along the beach. Sip on a refreshing rum punch on your complimentary beach chair. Dine on a delicious Caribbean lobster lunch. Lobster Lunch, Beverages, Beach Chairs are all included in the excursion.
What‘s Included
Local guide
GST (Goods and Services Tax)
Unlimited drinks (open bar)
Lunch
Authentic Sailing on a Historic Caribbean Sailing Vessel
Use of snorkel equipment & swim aids
Gratuities
Hotel pickup and drop-off
Options
Full Day Lobster Lunch
Lobster Lunch, Open Bar
Beach Chairs and Umbrellas,
Reviews
89 reviews
Total reviews and rating from Viator & Tripadvisor
Completely Magical
MicheleAltRock,Apr 14, 2026
- Review from Tripadvisor
5.00My husband and I love being out on the water. We knew that when we were planning a trip to Anguilla we would want to go on a boat excursion. So I reached out to our resort for some recommendations. They named Traditions - 5 star reviews all across the board. I contacted Deborah from Traditions with some questions and she wasted no time answering me (the customer service is unreal). We booked our Prickly Pear sail and waited for our trip to arrive. The day of our sail was perfect. The crew - Deborah, Thomas and Nash loaded us and two other couples on the beautiful boat and we set sail. Cocktails, snorkeling, an AMAZING lobster lunch, lounging on a gorgeous beach and swimming in the most picture perfect aqua water you have ever seen. The crew interacted with us the entire time and everyone truly had the best experience. I cannot say enough wonderful things. Book your excursion with Traditions and you will NOT be disappointed. 10/10.
Perfect Sailing Day
adsmerdel,Mar 27, 2026
- Review from Tripadvisor
5.00We had an amazing time sailing with the Traditions crew. Deb, Nash, and Thomas were fantastic and made the day truly special. The trip to Prickly Pear Island was beautiful—great lobster lunch, excellent snorkeling, and a perfect sail back. Highly recommend this experience if you’re visiting Anguilla!
Great trip
Jackie B,Mar 25, 2026
- Review from Tripadvisor
5.00My wife and I had a wonderful time on our sailing trip with Tradition sailing. The crew was great, the food was great. Overall a great experience. Highly recommend
Great sailing excursion!
216kareym,Jun 29, 2025
- Review from Tripadvisor
5.00This 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.
Another Great Sail to Prickly Pear
FloydFreedom,Apr 1, 2025
- Review from Tripadvisor
5.00This 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.
Great ride and amazing food and service
Howard V,Mar 28, 2025
- Review from Tripadvisor
5.00We 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.
Perfect day on the water
dar0sey,Feb 28, 2025
- Review from Tripadvisor
5.00Our 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.
A true trip highlight
CA NYC Traveler,Feb 7, 2025
- Review from Tripadvisor
5.00Fantastic 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.
A MUST DO
Etiennette Clamouze,Dec 13, 2024
- Review from Tripadvisor
5.00Deb, 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!
What a great day on the water !
Kenneth V,Jun 7, 2024
- Review from Viator
5.00This trip was a blast , captain and staff were the best . They made sure everybody was taken care off with drinks , food , etc.
From US$644.00
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Operated by Tradition Sailing Charters