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Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

icon 6 hours Mobile ticket Free Cancellation
Tickets from € 925.00

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May 2025
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You can select up to 12 travellers in total

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Adult (18 - 90)

Minimum: 1, Maximun: 12
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Child (4 - 12)

Maximun: 12
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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.
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  • Local guide
  • Unlimited drinks (open bar)
  • Lunch
  • GST (Goods and Services Tax)
  • Authentic Sailing on a Historic Caribbean Sailing Vessel
  • Use of snorkel equipment & swim aids
  • Gratuities
  • Hotel pickup and drop-off
Departure Point

6W25+9R8 Sandy Ground, Anguilla 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

Return Details

6W25+9R8 Sandy Ground, Anguilla 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

  • Tradition Sailing Charters, The Valley, Caribbean
    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.
    360 minutes
  • Prickly Pear Cays, Caribbean
    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.
    180 minutes
  • 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
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • 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 experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
Andrew J
22 Apr 2023
Fabulous day celebrating my wife’s 40th birthday party with friends and family through to sunset snorkelling jumping of cliffs great food Laurie ,Debs and the team fabulous hosts a wonderful day Thanks so much xxx
Joseph_C
21 Apr 2023
What a wonderful day in Anguilla, maybe my favorite day on our week long trip! The boat was incredibly unique and comfortable and the staff were friendly, attentive, and always helpful! Worth every penny!
DRBY310
14 Apr 2023
Another Great trip on Tradition. It’s a five star trip with five star folks I’m still full from my huge lobster lunch with all the sides. Worth twice the price.
This tour in Anguilla is organized by Tradition Sailing Charters

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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