Anguilla Romantic Sunset Sail: Ultimate Cocktail Hour Experience on a Classic Wooden Vessel
5.0
41 Ratings
Sandy Ground
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
(41 Ratings)
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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
636debbier636
Feb 17, 2024
A beautiful sunset sail - Once again Laurie, Deb and Dylan knocked it out of the park and provided an absolutely perfect Valentine’s Day sunset sail. The ambiance, guest interaction, drinks, nibbles, (especially the deviled eggs), and hosts made for a delightful evening. This is an absolute must do when you are on the beautiful island of Anguilla.
Review provided by Tripadvisor
Jay_k
Feb 17, 2024
A great crew - Being on the boat moving over the ocean feeling the breeze. An amazing sunset. Seeing the white goats on the cliffside A fun crew.
Review provided by Viator
Daniel_s
Jan 23, 2024
Great outing - Great crew, beautiful ship, free flowing cocktails, and delicious heavy appetizers. All in all an outstanding evening and experience.
Review provided by Viator
Cpalmer17
Jan 21, 2024
Beautiful cruise, find crew and guests! - Beautiful cruise. Delicious drinks and hors d’ouvres! Deb, Laurie (sp?), Hayden and Bella were lots of fun and right there to address any need. The boat itself is beautiful. A nice sized group of people…not too many, but enough to have great conversations and many laughs! Sunset was terrific, as was the return sail under the warm moonlit sky. Recommend highly!
Review provided by Tripadvisor
Llfgulfcoast
Jul 22, 2023
Beautiful sail with all the trappings…. - Fantastic experience from beginning to end. Thomas, Deb and crew were terrific…friendly, attentive, engaged. The sail was relaxing, the wine and champagne delicious and the hors d’oeuvres outstanding. Couldn’t have been a nicer evening. Well worth the money. Would highly recommend and would gladly repeat the experience.
Review provided by Tripadvisor
Juanse126gv
Jul 21, 2023
An extraordinary experience - My wife and I recently had the privilege of embarking on the breathtaking sunset sailing experience on board the Tradition; it was an absolute dream come true! From start to finish, the entire journey was filled with unforgettable moments, and I cannot praise the crew enough for making it a truly exceptional adventure. The crew members were an absolute delight from the moment we stepped on board. Their warm and welcoming personalities instantly put everyone at ease, and their passion for sailing and the beauty of Aguilla's coastline was evident throughout the trip. They were not only experienced sailors but also knowledgeable guides, sharing fascinating insights about the area's history and wildlife, which added an educational element to the journey. The boat itself was immaculate, and safety was clearly a top priority for the crew. I felt completely at ease, knowing that we were in capable hands. As we sailed gracefully along the coast, the crew ensured each passenger had a comfortable and enjoyable experience. They attentively catered to everyone's needs, and their level of professionalism was truly commendable. Oh, and let's not forget to mention the drinks served throughout the trip and the delectable hors d'oeuvres served while docked at Little Bay. They went above and beyond to treat us to a delightful assortment of gourmet bites that perfectly complemented the enchanting ambiance. We were lucky enough to see a couple of sea turtles pop their heads out of the water and a variety of sea birds nesting along the cliffs of Little Bay. I cannot recommend this sunset sailing experience in Aguilla enough and we are already looking forward to next year's full-day adventure.
Review provided by Tripadvisor
Getaway27413334064
Jun 29, 2023
Sunset Sail - Great experience all around. Lovely sailboat, friendly staff, lots of drinks and gourmet appetizers. Highly recommend.
Review provided by Tripadvisor
Suzannering374
Jun 26, 2023
Fabulous Experience - If you have the privilege to visit Anguilla you MUST book a charter with Deb and the crew. It was a fantastic experience. Food was delicious. Cocktails flowing. Plenty to drink if you prefer an alcohol free trip. And they offer options for people with food allergies. Amazing time! Do not think twice…you won’t be disappointed. Thank you Traditions for making the Sunset a beautiful moment on our trip.
Review provided by Tripadvisor
O8101kusarar
Jun 8, 2023
Super Fun - This was a great way to end our trip in Anguilla! The crew provided charcuterie and drinks. They kept them flowing all night. The crew recognized us from a previous snorkel trip. They are so friendly and lovely. We had a great time!
Review provided by Tripadvisor
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up to 12 guests
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May 2024
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