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Select Date and Travelers

from $290.00 USD

Nov 09, 2019
Number of Travelers

Number of Travelers

Adult 18 - 90 years


Child 4 - 12 years


Available Options

Please select the date and travelers first to check availability.

No options are available based on selected date and travellers numbers/types.


  • 6 hours (Approx.)
  • Hotel pickup offered
  • Mobile ticket
Overview Overview

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.

Inclusions & Exclusions Inclusions & Exclusions
  • Authentic Sailing on a Historic Caribbean Sailing Vessel
  • Mimosas & Freshly Squeezed Orange Juice
  • Unlimited drinks (open bar)
  • Use of snorkel equipment & swim aids
  • Bottled water & non-alcholic drinks
  • Lunch
  • Tradition's Signature Cookies
  • Fresh Watermelon
  • Local guide
  • Snacks
  • Bottled water
  • Alcoholic Beverages
  • Gratuities
  • Hotel pickup and drop-off
Departure & Return Departure & Return
Departure Point

Sandy Ground Dinghy Dock

Departure Time

9:00 AM


See Availability

What to Expect What to Expect

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.

The tender/dinghy will be at the Sandy Ground Dinghy Dock at 9 am to pick you up and transport you to Tradition anchored in the bay.  The crew will greet you with Morning Mimosas or a glass of freshly squeezed orange juice. After a short safety briefing and a bit of history of Tradition's life as a Caribbean sail-trader and rum smuggler, we'll top off your mimosas and cast off the mooring lines. Once we get underway for Prickly Pear, guests can help us raise the sails or simply relax on our spacious deck 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. 

The sail to the gorgeous Prickly Pear Cay, is approximately 1.5 hours.  Once at anchor, discover the underwater magic that exists below the surface as you snorkel Anguilla’s reefs which are teeming with tropical fish.nAfter a fantastic snorkel or swim, enjoy a refreshing cocktail at the beach bar before lunch where you can try feeding banana-quit birds from the palm of your hands. Then at around 12:30, feast on succulent grilled Caribbean lobster (Chicken, Ribs, Fish or Vegetarian also available), in shaded comfort at the  beach restaurant.

After lunch, there will be ample time for more snorkeling, walking Prickly Pear’s pristine white sandy beach in search of the perfect shell, or exploring the rocky nesting grounds of indigenous Brown Boobies and seagulls. At about 1:30 we will make our way back to Tradition and depart Prickly Pear by 2 to begin our afternoon sail back to Anguilla. The 1.5 hour sail to Sandy Ground is the perfect opportunity to try steering with Tradition's massive hand carved tiller and test your skills against the wind. 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.

Hotel Pickup Hotel Pickup

Hotel pick-up is offered for this tour. Note: if you are booking within 24 hours of the tour/activity departure time, we cannot guarantee hotel pick-up. Once your purchase is complete, we will send you complete contact information (phone number, email address, etc.) for our local operator to organize pick-up arrangements.

Additional Info Additional Info
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • 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
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 12 travelers
Cancellation Policy Cancellation Policy

For a full refund, cancel at least 24 hours in advance of the start date of the experience.


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