The Best Sunset Sail and Cocktail Hour in Anguilla

carribean » anguilla » anguilla » anguilla

From $229.00

19 reviews   (5.00)

Price varies by group size

Lowest Price Guarantee

Pricing Info: Per Person

Duration: 2 hours

Departs: anguilla, anguilla

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

Learn more


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.

What's Included

Alcoholic Beverages

All Fees and Taxes

Bottled water

Hors D'oeuvres Dinner on the deck of Tradition


What's Not Included


Traveler Information

  • ADULT: Age: 18 - 99

Additional Info

  • COVID-19 vaccination required for guides
  • Face masks required for travellers in public areas
  • Guides required to regularly wash hands
  • Must be 18 years or older
  • Regular temperature checks for staff
  • Social distancing enforced throughout experience
  • Transportation vehicles regularly sanitised
  • Contactless payments for gratuities and add-ons
  • Face masks required for guides in public areas
  • Gear/equipment sanitised between use
  • Hand sanitiser available to travellers and staff
  • Paid stay-at-home policy for staff with symptoms
  • Regularly sanitised high-traffic areas
  • Suitable for all physical fitness levels

Cancellation Policy

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

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Experience may be cancelled due to Insufficient travelers
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.


Perfect evening!
katherinecC3115TW, 04-08-2022
My husband and I took the sunset sail and it was wonderful!!! Thomas and Pepper were so fun and went out of their way to ensure our trip was memorable. Highly recommend this activity!!!!
What a great experience...
Kayla_P, 21-05-2022
What a great experience that will be remembered for a lifetime! Words do not do this experience justice, as we were swept away with how special it truly was. The crew, drinks, snacks and trip were all equally amazing. Highly recommend.
Don’t Miss This Unique Experience
petesdad, 12-05-2022
The time with Deb, Thomas and Pepper was amazing and our chef put a wonderful table together in the middle of the ship. The character of the experience was unbelievable !
A special evening
kennys235, 21-04-2022
What a wonderful evening aboard Tradition! The crew of Laurie, Deb, Thomas, and Pepper did everything to make the evening as pleasant as possible. I've done this sail a couple times in the past, and it keeps getting better each time! Tradition is a special sailboat, and the history as to why is explained. It is kept in meticulous shape and lovingly cared for by Laurie and Deb. The food and beverages are top notch, especially the cheeses! Very well appointed indeed. Guests are made to feel so comfortable, and we are all soon chatting as having been friends for years. This happens because of the warmth and friendly nature of the crew making everyone feel so at ease. The knowledge the crew has of the sea and wildlife adds to the experience. Relax and enjoy a special evening!
Wonderful experience
Naycsak, 11-04-2022
Great trip.First class. Deb and Lorrie were great hosts and very knowledgeable seafarers and shared history of the island and surrounding islands. They even had their newly promoted captain Charlie sailing the boat.The 10-2 tour was wonderful despite the rain and winds(which was a little scary). Drinks flowed the entire time, The mimosas with fresh orange juice were refreshing as we got on board. Rose, beer and rum punch too. Equipment was supplied for snorkeling(except vests, used noodles and they worked well.). The lunch was delicious. All the food was homemade. The sandwiches with big lobster chucks and salad and big chocolate chip cookies were all delicious. It was nice that there was just 8 people on the sailboat.

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