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: 24 hours
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….
What's Included
  • Dinner
  • Alcoholic beverages
  • Carbonated beverages
  • Bottled water
  • All Fees and Taxes
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…
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…

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
(63 Ratings)
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Emilyb685
Jul 22, 2025
Wonderful wedding weekend sail - We requested a private sail for our wedding weekend ( 14 people total). Upon a arrival to the boat, there was a juat married sign and champagne cocktails. We had a wonderful sail, the crew is so welcoming and always checking on the guests to make sure their drinks are full and everyone is having a good time. This is the second time I've sailed on the Tradition and would recommend to anyone visiting the island.
Review provided by Tripadvisor
256darcyw
Jul 18, 2025
- Deb and Thomson were friendly and did a great job making sure we were enjoying ourselves and their service was excellent! The food was delicious and champagne cocktails were flowing the whole time. The 2 hours spent sailing around the different sites was relaxing with beautiful scenery. The sunset was gorgeous and we met two interesting and friendly couples as well. Highly recommend this excursion.
Review provided by Tripadvisor
Anthony_c
Jun 18, 2025
Beautiful - What an amazing evening. Deb and her crew take care of everything. Come hungry and be prepared for a great evening with stunning views,
Review provided by Viator
Annewaldron
Jun 3, 2025
Absolutely a Must-Do - 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 never empty. The sailing was exhilarating with such beautiful coastline views. We moored at the rocky cliffs of Little Bay and the spread of charcuterie was bonkers amazing. We saw a spotted eagle ray, several sea turtles, and a number of beautiful birds, including a white tailed tropic bird (it's late for them so we were lucky). We just could not recommend this experience enough—it was truly a highlight of our beautiful trip to this beautiful island.
Review provided by Tripadvisor
Travel05898667762
May 1, 2025
A wonderful cruise! - 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 doeurves, and plenty of drinks of whatever people might want to keep us happy and smiling. It was ideal that they had a maximum of 12 people on board which was a nice size to socialize with others or not. It was a beautiful and relaxing cruise, though cloudy enough to miss out on a great sunset … but that didn’t matter, it was an incredible experience!
Review provided by Tripadvisor
Chrisv806
Apr 1, 2025
A Totally Pleasurable Sunset Cruise - 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 boat has a tremendous history and is immaculately kept up. The skill and experience of the crew was readily apparent. Highly recommended!
Review provided by Tripadvisor
636debbier636
Mar 17, 2025
The best there is. - 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 better. Thanks for a wonderful evening.
Review provided by Tripadvisor
Mrbvermont
Mar 8, 2025
Fun Evening - 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 views and sunset. It was just spectacular. The crew was outstanding. Could not have had a better time. Thanks.
Review provided by Tripadvisor
Crunchyjiff
Feb 28, 2025
Memorable sunset experience - What a lovely way to enjoy our last evening on the island. We enjoyed learning about the history of the Tradition as well as points of interest while we cruised along the coastline. The smaller group on our shared sail allowed for meeting new people and a relaxing vibe. The Champagne cocktails and light bites were a level up — this happy hour is hard to beat. Big thanks to Capt. Laurie, Deb, and Marie for their hospitality!
Review provided by Tripadvisor
Tttsunshine
Feb 26, 2025
Magical in EveryWay - Magical beautiful experience on this Red Beauty Vessel ! Truly the biggest highlight of our trip. Top Notch 5 Star⭐️⭐️⭐️⭐️⭐️ service from start to finish! Highly recommend!
Review provided by Tripadvisor