The Best Sunset Sail and Cocktail Hour in Anguilla

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The Best Sunset Sail and Cocktail Hour in Anguilla

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 US$390.61  per guest
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Adult x1
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Instant Confirmation
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Earliest available date: November 23, 2026
Free cancellation (24 hours notice)
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For each guest that attends this experience, byFood will donate
10 meals
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

Experience a captivating sunset sail along Anguilla's coast on a classic wooden vessel. Enjoy cocktails, romance, and stunning views, perfect for couples and star-gazing enthusiasts.

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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

Carbonated beverages
Soda/Pop
Bottled water
Alcoholic beverages
Alcoholic Beverages
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.

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Reviews
5.0
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based on 68 reviews
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Spectacular Sunset Sail
July 02, 2026

Booked Traditions Sunset Sail for my birthday and it could not have been better. We had an amazing time and the perfect way to end a day in Anguilla. Deb, Laury, and Nash were the perfect hosts and...read more

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Top Notch Sailing Adventure
June 17, 2026

The crew and overall experience was fantastic! We had a wonderful time! This is an experience you don’t want to miss! We will book with them again on our next trip to Anguilla!

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Sunset sail
April 08, 2026

This was our second experience on tradition, having done the snorkeling trip last year. The cruise was lovely and the food and drink were abundant and delicious! The crew are knowledgeable, experie...read more

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Sunset sailing with Deb-- Magic!
March 22, 2026

Wow! Just a great decision to do this sail during our 6th trip to Anguilla-- wish we had done this before! In talking with others onboard, many book it every time they are on island. Beautiful boat...read more

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Great Sunset Sail Experience
February 17, 2026

We had a beautiful sunset sail with Deb and the very friendly crew. Loved the old historic schooner. Plenty of cold beverages and great appetizer spread. Would definitely go again.

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