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Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

83 Reviews 5.00 out of 5 stars Based on 83 reviews collected by City Boat Tours and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
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Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Anguilla, Anguilla
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from US$644 per person

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Sailing to Prickly Pear
Delicious Caribbean Lobster Lunch
Fishing is part of the adventure!
Tradition at anchor at Prickly Pear Cay
Traditional Sailing Adventure to Anguilla's Prickly Pear Cays Image 5

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6 hours (approx.)
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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.

What's Included

  • Lunch
  • Unlimited drinks (open bar)
  • GST (Goods and Services Tax)
  • Gratuities
  • Hotel pickup and drop-off
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Meeting Location

Meeting point

6W25+9R8 Sandy Ground
Anguilla

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

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.
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6 hours • Admission Ticket 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.
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3 hours • Admission Ticket Included

Additional Info

  • Confirmation is instant and will be received at time of booking
  • Not recommended for travelers with serious shellfish or nut allergies
  • 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
  • This tour/activity will have a maximum of 12 travelers

Frequently Asked Questions

(8)

Q: Will I get seasick on Traditional Sailing Adventure to Anguilla’s Prickly Pear Cays?

A: If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy. Read more Feb 2023

Cancellation Policy

You can cancel up to 24 hours in advance of the tour for a full refund.

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Activity code: C-43363P3

Traveler Photos

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Reviews

5.00
83 reviews

Average 5.00 out of 5 stars based on 83 traveler reviews collected by City Boat Tours and partner sites such as Cool Destinations and TripAdvisor

5 stars
83
4 stars
0
3 stars
0
2 stars
0
1 star
0

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Frequently Asked Questions (8)

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

The answers provided below were previously given in response to questions from City Boat Tours customers.

Filter by:

Q: Will I get seasick on Traditional Sailing Adventure to Anguilla’s Prickly Pear Cays?
A:

If you have any doubts about becoming seasick on the water, we recommend taking a Dramamine® Motion Sickness Relief tablet the night before your trip. Some people recommend taking it the night before your cruise and then again that morning so you will not feel so drowsy.

Feb 2023
Q: What is the cancellation policy for the Traditional Sailing Adventure to Anguilla’s Prickly Pear Cays?
A:
You can cancel up to 24 hours in advance of the tour for a full refund.
  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (AST).
  • This tour 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.
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Lunch.
  • Unlimited drinks (open bar).
  • GST (Goods and Services Tax).
  • Authentic Sailing on a Historic Caribbean Sailing Vessel.
  • Use of snorkel equipment & swim aids.
  • Local guide.
The following is NOT included:
  • Gratuities.
  • Hotel pickup and drop-off.
Apr 2025
Q: What is the weather cancellation policy?
A:

This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Apr 2025
Q: What is the minimum age for this tour?
A:

The minimum age to participate is 4. This tour requires at least one adult to accompany children..

Apr 2025
Q: My date is not available in the calendar, I am just checking to see if it is available?
A:

If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

Apr 2025
Q: Is this an accessible tour?
A:

Accessibility information for the Traditional Sailing Adventure to Anguilla's Prickly Pear Cays is as follows:

  • Not recommended for travelers with serious shellfish or nut allergies
  • Suitable for all physical fitness levels
Apr 2025
Q: Where is the meeting point for this activity?
A:

Detailed check-in instructions – including meeting point address, Google map, and parking information – for Traditional Sailing Adventure to Anguilla's Prickly Pear Cays will be included in your confirmation email from City Boat Tours. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

 

 

Mar 2024

What's Included

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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

Additional Info

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

  • Confirmation is instant and will be received at time of booking
  • Not recommended for travelers with serious shellfish or nut allergies
  • 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
  • This tour/activity will have a maximum of 12 travelers

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

Lowest Price Guarantee

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on City Boat Tours and 48 hours before your trip starts, we will refund the difference.
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Free Cancellation

American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

100% refund
No refund

You can cancel up to 24 hours in advance of the tour for a full refund.

  • For a full refund, you must cancel at least 24 hours before the tour start time.
  • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the tour start time will not be accepted.
  • Cut-off times are based on the tour local time (AST).
  • This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This tour 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.

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American Museum of Natural History Admission Ticket

American Museum of Natural History Admission Ticket

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