The Best Sunset Sail and Cocktail Hour in Anguilla

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Summary
Experience Details
What You’ll Experience
Where to Meet
Reviews
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Duration
2 hours 30 minutes
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Number of Guests
1 - 12 guests
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Language
English
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Digital Ticket
Mobile or paper ticket accepted

Join us for an unforgettable sunset sail along Anguilla's coast. Enjoy champagne cocktails, share stories, and marvel at breathtaking views on a classic wooden vessel.

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For each guest that attends this experience, byFood will donate
10 meals

Experience Details

The Ultimate Sunset Sail Experience. If you've never sailed on a classic wooden vessel, our Sunset Sail on Tradition is the way to start. Sail with us (yes, we'll be raising those sails all by hand, using traditional block and tackle rigging) along Anguilla's coastline. We'll keep your Champagne Cocktails & other beverages topped up while sharing the history of the boat and Anguilla. As our sunset sail caters only to adults its the perfect sailing excursion for honeymooners, romantic, and anyone wishing to experience the joys of sunset sailing.


You'll find yourself meeting new friends. The soft rosy light of the late afternoon sun will entice the photographer in you. And the charm of the wooden deck and the wind in the sails will live in your memory forever. As we sail back under the night sky, keep watch for satellites and at least one shooting star to wish on.

Sample Menu

MAIN
A selection of fine French Cheeses
served with a variety of crostini and rice crackers
MAIN
Roasted gorgonzola stuffed, bacon-wrapped figs in a balsamic glaze
MAIN
Charcutere Platter with a selection of saucisson
served with a selection of cornichon, mixed olives, and french dijon
MAIN
Classic Devilled Eggs
Such a crowd pleaser, we don't dare take it off the menu
MAIN
House-made Hummus
Ground sesame paste, chickpea, lemon, garlic & cumin
MAIN
House-made Olive Tapenade
kalamata olives, parsley, capers, lemon, garlic, olive oil
MAIN
Guava & Sorrel Pepper Jelly
the perfect sweetly hot kick to accompany our hors d'oeuvres

What You Get

All Fees and Taxes
Carbonated beverages
Soda/Pop
Bottled water
Gratuities

Good To Know

  • Suitable for all physical fitness levels
  • Must be 18 years or older

What You’ll Experience

There is nothing that says unforgettable Caribbean vacation than "Cocktail Hour" on an historic Caribbean Rum-smuggling sailboat. Step aboard Tradition and sail with us along the Anguilla coastline while enjoying our signature Champagne Cocktails, premium open bar, and tucking into our delicious house-made hors d'oeuvres. This intimate sail, on one of the last remaining sailing vessels of her kind, is an unforgettable highlight on your Anguilla vacation. With a maximum capacity of 12 passengers there is plenty of space to social distance while getting to know other Anguilla visitors. While we sail into the sunset, take advantage of the perfect light of the fading afternoon sun on the sails to capture some amazing photos. During this 2.5 hour sail along the Anguilla coastline, weaving our way between Crocus Bay and Little Bay, our friendly and professional crew will be making sure your drinks are always topped up, and the conversation keeps flowing. We're always happy to share some Anguilla history and stories. We'll keep a lookout for turtles, dolphins and if we're lucky during their migration, humpback whales passing through to their Spring and Summer waters.

Meeting & Pickup

Meeting Point

6W25+7R Sandy Ground, Anguilla, AI, 2640

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We will pick you up at the Sandy Ground Dinghy Dock in the center of Sandy Ground.
End Point

This experience ends at the meeting point.

Cancellation Policy

Cancel your booking at least 24 hours before the experience start time to receive a full refund minus a 3.2% transaction fee.

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What People Are Saying
Overall ratings and reviews
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(60)
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Absolutely a Must-Do
June 03, 2025
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(TripAdvisor)

This experience vastly exceeded our expectations. The crew were amazing and attentive—we started with a champagne cocktail and toasted a newlywed couple who joined us, and our wine glasses were nev...read more

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A wonderful cruise!
May 01, 2025
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(TripAdvisor)

Four of us took a Sunset Cruise on April 30 and had an absolutely great time! Captain Laurie and his two person crew were incredibly welcoming, kept us very safe, and served up delicious hors doeu...read more

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A Totally Pleasurable Sunset Cruise
April 01, 2025
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(TripAdvisor)

An excellent sunset cruise provided by the Tradition team! Safety first, and the crew was continuously attentive to everyone's needs. We anchored in a calm cove for a meal watching the sunset. The ...read more

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The best there is.
March 17, 2025
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(TripAdvisor)

Laurie, Deb and team are the best. Safety, professionalism, fun and a great sailing experience each and every time. Add beautiful weather, great drinks and food and it really doesn’t get any bett...read more

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Fun Evening
March 08, 2025
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(TripAdvisor)

Six of us, three cousin's and our wives, went on an amazing sunset cruise on Traditions. Everything was wonderful from the dock pick in the dingy to the cocktails and appetizers to the amazing view...read more

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from  $394.21 
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Please note that the time is in Atlantic Standard Time.
Free cancellation (24 hours notice)
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INSTANT CONFIRMATION
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Earliest available date: June 23, 2025
from  $394.21  per guest
Book Now
Please note that the time is in Atlantic Standard Time.
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals