Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

Overview

Available languages

English

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‘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

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.

6 hours • Admission Included

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.

3 hours • Admission Included

Options

Full Day Lobster Lunch

Lobster Lunch, Open Bar
Beach Chairs and Umbrellas,

Reviews

5.00

86 reviews

Total reviews and rating from Viator & Tripadvisor

Great sailing excursion!
216kareym,
Jun 29, 2025
- Review from Tripadvisor
5.00
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.
Another Great Sail to Prickly Pear
FloydFreedom,
Apr 1, 2025
- Review from Tripadvisor
5.00
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.
Great ride and amazing food and service
Howard V,
Mar 28, 2025
- Review from Tripadvisor
5.00
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.
Perfect day on the water
dar0sey,
Feb 28, 2025
- Review from Tripadvisor
5.00
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.
A true trip highlight
CA NYC Traveler,
Feb 7, 2025
- Review from Tripadvisor
5.00
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.
A MUST DO
Etiennette Clamouze,
Dec 13, 2024
- Review from Tripadvisor
5.00
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!
What a great day on the water !
Kenneth V,
Jun 7, 2024
- Review from Viator
5.00
This trip was a blast , captain and staff were the best . They made sure everybody was taken care off with drinks , food , etc.
Just book it - NOW!!
caitlinmoyna,
May 20, 2024
- Review from Tripadvisor
5.00
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!
Definitely worth the wait!
Mary D,
May 10, 2024
- Review from Tripadvisor
5.00
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.
Perfect sailing day
JordanaS1000,
May 8, 2024
- Review from Tripadvisor
5.00
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.