Anguilla Romantic Sunset Sail: Ultimate Cocktail Hour Experience on a Classic Wooden Vessel

Experience the ultimate romantic sunset sail on a classic wooden vessel in Anguilla. Sip Champagne Cocktails, learn about the boat’s history, and create lasting memories under the night sky.

Duration: 2 hours, 30 minutes
Cancellation: 1 day learn more
Highlights
  • 6W25+7R Sandy Ground - 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.

What's Included
  • Carbonated beverages
  • Bottled water
  • Dinner
  • All fees and/or taxes
  • Alcoholic Beverages
What's Not Included
  • Gratuities
Meal Options
  • A selection of fine French Cheeses - served with a variety of crostini and rice crackers
  • Roasted gorgonzola stuffed, bacon-wrapped figs in a balsamic glaze
  • Charcutere Platter with a selection of saucisson - served with a selection of cornichon, mixed olives, and french dijon
  • Classic Devilled Eggs - Such a crowd pleaser, we don’t dare take it off the menu
  • House-made Hummus - Ground sesame paste, chickpea, lemon, garlic & cumin
  • House-made Olive Tapenade - kalamata olives, parsley, capers, lemon, garlic, olive oil
  • Guava & Sorrel Pepper Jelly - the perfect sweetly hot kick to accompany our hors d’oeuvres
Additional Information

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.

  • Must be 18 years or older
Location
6W25+7R Sandy Ground
We will pick you up at the Sandy Ground Dinghy Dock in the center of Sandy Ground.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
5.0
(48 Ratings)
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Michele310c
Jul 2, 2024
Sunset Cruise - Tradition is AMAZING! The drinks, food & hospitality are perfect! Amazing crew! I look forward to sailing with them again!
Review provided by Tripadvisor
David_b
Jun 28, 2024
The BEST sunset cruise - Amazing service. Excellent drinks — started with passion fruit and mandarin vodka with Cointreau served in a brown sugar rimmed flute. Delicious rum punch? Of course! Beer and wine? Yes. Water and soda too. Food was a well-curated selection of high end cheeses, salami, bacon wrapped figs, olive tampenade, hummus, deviled eggs. WOW. Cruise was two hours of pure delight.
Review provided by Viator
859debd
Jun 15, 2024
Great excursion small group. Friendly crew - The sail was terrific. The crew especially Deb were amazing. There were only 6 of us on the excursion, and nice small group. Once on board, they served a great cocktail and continued to offer to keep your glass filled. The food was great and plenty of it. Highly recommend sailing with Traditions.
Review provided by Tripadvisor
Bfarris2024
Jun 11, 2024
Great Sunset Sailing - Very nice sunset sail. The ship was very clean and comfortable. The sunset sail was very enjoyable and one of the highlights of our trip to Anguilla.
Review provided by Tripadvisor
J8785stsusanm
Jun 2, 2024
Friendly, easy-going sail on a gorgeous sloop - Laurie and Deb, and their magnificently cared for sailboat Tradition are a must-do while in Anguilla. Laurie regaled with history and interesting stories about the island. They brought us out to Little Bay to see the rock formations, serving a delicious spread of hors d’œuvres and endless punch. A perfect way to end out a day on this beautiful island.
Review provided by Tripadvisor
Dcathoops
Jun 1, 2024
Believe all the reviews! - Believe all the reviews you see here on TA. The boat is beautiful, the crew is wonderful, food and drinks were top notch. I love taking sunset cruises,but my wife was a little nervous about 2.5 hours, but it was fantastic. She loved it. Laurie and Deb were tremendous hosts with great stories of the history of Anguilla and their own personal history as well. Well worth the cost
Review provided by Tripadvisor
Catcarter115
May 27, 2024
Amazing Evening. - Amazing sailing experience with Deb and Laurie. First class experience and service. The beverages were unlimited and the small bites food was a lovely presentation and delicious.
Review provided by Tripadvisor
Taralp4756kt
May 7, 2024
Amazing Sunset Cruise of Anguilla! - The most amazing sunset sail! We would truly recommend to everyone. I contacted Deb last minute and she was able to accommodate our group. Thomas was super knowledgeable about the island and Baya had prepared delicious Hors D'oeuvre that were a hit. The open bar was definitely a plus! We will definitely be sailing with Tradition when we return to Anguilla!
Review provided by Tripadvisor
Laurie767
Apr 24, 2024
Long Time Visitors Have a great Evening on the Water - We've been going to Anguilla for over 30 years (to a spot with a great sunset view) and never felt compelled to take a sunset cruise. This year my adult daughter and her husband (he is a first timer to Anguilla) came for a visit and I decided it might be fun for him to get to see more of the island. Additionally, we invited family friends who basically call Anguilla a second home. I was surprised at what a unique experience Traditions provides, from the historical aspect of the boat itself to giving even jaded visitors another way to view Anguilla. It was a fantastic evening out on the water. Laurie and Deb provide everything necessary for a perfect sail. Pelicans, gorgeous coastline and wonderful drinks and snacks made for a terrific evening! I highly recommend, even for long time Anguilla visitors!!
Review provided by Tripadvisor
Mrbvermont
Mar 19, 2024
Sunset Cruise in Anguilla - My wife and I had a wonderful experience on the traditions sunset cruise. We enjoyed everything the crew, drinks, food and fellowship with the other passengers. It was an absolutely wonderful experience we would defiantly go again and recommend this trip to others. It was really fun!
Review provided by Tripadvisor
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up to 12 guests
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September 2024
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