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
(80 Ratings)
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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
E9762nnbobm
Apr 17, 2024
Another Prickly Pear Day in Anguillan Paradise - This was our second Prickly Pear Cay day sail with Tradition. Our first trip, during a visit to ex-pat friends in Anguilla, was amazing. This repeat trip for the four of us was every bit as good, and possibly even better due to our relative familiarity with what to expect. With an initial greeting at the dock at Sandy Ground at 9 o'clock in the morning, a short dinghy ride out to Tradition - a magnificent and lovingly preserved wooden sailing ship constructed by hand, and welcome mimosas (or fresh squeezed OJ for those not imbibing so early in the morning), the kickoff to the day's journey was flawless. Our departure from Sandy Ground harbor was preceded by a thorough safety briefing by Captain Laurie. His breadth of Anguillan and Caribbean sailing, commerce, shipbuilding, and bootlegging history is boundless, and he was generous in sharing his knowledge with us. Along with Captain Thomas and Deb, our experienced first mate and guest services director, our foursome and seven other instant best friends were in capable and safety conscious hands. Once out of the harbor, the sails were hoisted and the engine was cut. We experienced the beautiful soothingly quiet sounds of the sea and the wind, the sights around us from the sea spray to the far off horizon, and the feel of the powerful ocean beneath our feet as the breeze and sun enveloped us. We sailed along briskly and Tradition heeled over gently under 100% wind power. The sun shone down and the warm sea breeze enveloped us. Not a care in the world! The fun was non-stop, as were the provisions (including libations, alcoholic and not), which were available all day long. As we turned between two small spits of land to approach Prickly Pear Cay, we saw large numbers of brown boobies and their light-colored baby chicks, a welcome sight that we were told signaled the rejuvenation of their local population. Reaching Prickly Pear Cay, an uninhabited island with beach chairs, island tunes, and a kitchen for day visitors, we anchored off shore and settled in for some serious snorkeling along the extensive reef system that lies just off shore. Coral of every description - sadly experiencing the bleaching that is being seen worldwide - was the backdrop for a variety of brightly colored fish. Last year, jellyfish were everywhere, and we were happy to not see them this time. Near shore, there were many yellowtail snapper cruising in the shallow water above the fine sandy bottom. Lunch was either Anguillan lobster or ribs. Last year, my wife and I went half-sies, but this year all four of us had the lobster. It did not disappoint! It was prepared perfectly, served hot, and tasted absolutely scrumptious with sides of slaw, rice and beans, and curried potatoes. After a little siesta time in the sun with a bright green rum punch, a game of cornhole on the beach, or sitting in the shade provided by low-hanging fronds of the beach palm trees - my preference - we swam or snorkeled back out to Tradition to prepare for the sail back to Sandy Ground. We were treated to fresh fruit and giant home-baked chocolate chip cookies on the return sail. As the mid-afternoon sun drifted slowly toward the west, we saw Sandy Ground coming slowly into view, signaling the end of another Prickly Pear day in the paradise called Anguilla.
Review provided by Tripadvisor
Matthew_l
Mar 26, 2024
Don’t hesitate…book it! - The entire crew is so knowledgeable and accommodating. They treated us like family during our entire charter. We brought our young kids and they also had an amazing experience. They keep talking about Prickly Pear and the amazing lunch.
Review provided by Viator
Mcclellan77
Mar 24, 2024
Amazing Sailing Adventure! Highly Recommend - The boat crew was very accommodating and made our sailing adventure comfortable, safe, and memorable! We would highly recommend any families looking for a boating experience in a smaller group with an amazing staff! On our trip, we snorkeled near the Prickly Island and saw two stingrays! After our lunch on the island, we jumped back on the boat to enjoy snacks, watermelon, and cookies! And we even caught a barracuda on the fishing line traveling back to Sandy Ground! Thank you to the staff for making this an adventure our family will remember forever.
Review provided by Tripadvisor
Lianedavey
Mar 10, 2024
Perfect Paradise on Prickly Pear - This was the perfect day! Laurie, Deb, and Dylan created such a warm and fun experience where every last thing was thought of. We had a great cruise, fun snorkelling with many beautiful fish, an amazing feast of lobster, and the yummiest chocolate chip cookies on the way home. It was especially nice to actually sail rather than running under motor! I would highly recommend Tradition to anyone.
Review provided by Tripadvisor
Jake_n
Jan 31, 2024
Don’t miss this! - Definitely take this tour as the boat, captain, mate, and crew were beyond professional, friendly, knowledgeable, safe, clean, etc. can’t say enough good things about it. Grilled lobster lunch was great too! And the cookies!
Review provided by Viator
Aileen
Jan 12, 2024
A true delight! - Oh man, what a delight this day trip was! Thanks to Deb, Dylan and Thomas for being the best crew ever. The boat is gorgeous, if you’re lucky you can help hoist some stuff and feel like a sailor! The lunch at Prickly Pear was DELISH. If you want easy, chill vibes, gorgeous views and fun snorkeling with a bomb meal to boot? The Tradition is for you! Ahoy!
Review provided by Tripadvisor
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up to 12 guests
1 Adult
November 2024
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