Tradition Sailing

If you’ve ever wanted to experience sailing amidst the cerulean blue waters of the Caribbean, Tradition Sailing can make this dream come true. Tradition Sailing has made a name for itself as a premier provider of chartered sailing experiences. Come see why so many enjoy and keep coming back to Tradition Sailing.

Sailing Adventures

Tradition Sailing offers several sailing adventures. There is the popular Sundowner Sailing Cruise where you’ll get to experience the beauty of a Caribbean sunset in this 2.5-hour cruise. Sit back and enjoy the delicious hors d’oeuvres and beverages as you sail to Little Bay. You get to stop at the cliffs where you’ll get to see the beautiful sunset. The Prickly Pear Lobster Lunch Day Sail combines an enjoyable 1.5-hour sailing experience to Prickly Pear that includes a lobster lunch, delicious snacks and beverages and snorkel gear for exploring at Prickly Pear. For those that are interested in a more private sailing experience, Tradition Sailing does offer private excursions which include full-service catering and a variety of other extras. This option is perfect for those special occasions such as wedding ceremonies, photo shoots or simply if your want to build your own private sailing experience.

Sailing Packages

By offering several sailing packages, Tradition Sailing makes it possible for you to enjoy the experience of sailing in Anguilla. The company offers sailing packages at various rates as well as at various lengths, so you can choose the sailing experience that you most desire. Tradition Sailing has received The Certificate of Excellence from TripAdvisor multiple years in a row because of their dedication to providing a premier sailing experience. It is for this reason that they continue to hold the title as Anguilla’s #1 Sailing Adventure.

Booking Your Trip

Booking a sailing trip with Tradition Sailing is simple. You can use the online reservation form and calendar to locate and book the sailing package of your choice. Available booking information includes full details for all of the available packages such as the name, location of sail as well as the time length of the applicable sail. You can view the calendar to find the best dates for an upcoming sail.

For more information about Tradition Sailing, contact the company directly at 264.476.7245, email them at

Make your trip to Anguilla memorable by using Refined Retreats for your lodging needs. We offer exceptional, luxury accommodations that are sure to add to the joy of your Anguilla vacation. To book your vacation rental today contact us directly at +1 264-476-7245 or visit us at