Luxury and Adventure.

Book online or call +1.264.476.7245 to reserve your amazing tropical experience.

Exclusive Private Excursions

Indulge in your very own private adventure and romance on azure seas. We’ll sail you to pristine snorkeling sites and breathtaking reefs where dolphins swim and sea turtles dwell.

Half Day Sailing and Snorkeling Adventure

Join us for a magnificent sail to where a tropical paradise awaits. It’s a day of indulgence that begins the moment your feet touch the deck of Tradition and only ends when we wave you goodbye.

Deluxe Sunset and Starlit Cruise

Our Deluxe Champagne & Tapas Sunset Cruise is an inspired blend of spectacular scenery & stunning sunsets, a delicious selection of tapas on deck of our historic trading vessel, and the splendor of sailing under the stars.

A Classic West Indian Sloop

This vacation, create a new tradition…


Photo Galleries

What others say about us

“Trust me….you REALLY want to do this”
5 of 5 starsReviewed May 31, 2013

Even if your plan for Anguilla includes nothing more than: beach, pool, beach bar, dinner, repeat….you must fit in a trip on the Tradition. Step aboard the beautiful 50′ Carriacou sloop and be greeted with warm muffins and cold champagne. They offer day trips to Prickly Pear, half day trips to Little Bay and Sunset cruises. We took the half day charter to Little Bay. My wife and I had the added benefit of being the only guests booked….hello private charter! We were immediately impressed that they went ahead with the charter with just the two of us.

The crew, headed by Capt. Laurie, were professional, capable and terrifically hospitable. Deb, Brennon and Erica took great care of us. Beer? Yes, please. Wine? Sure. Rum punch? Why not. Sailing, swimming, sunning….just a fantastic morning. Around 12:15, Deb announced that the charter was “officially” over. They didn’t have an afternoon trip, so she asked if we were in any hurry to get back. Um, no…..I’ll have another rum punch, please! So, we spent the next couple of hours just chatting with our new friends and having an all-around great time.

Back to Sandy Ground. With all the work out of the way, the crew is finally able to enjoy a cold beer with us. Cheers, ya’ll!

BooZoo(excerpt from

Eleven of us took the lunch trip to Prickly Pear island on “Tradition”. She is a West Indian wooden sloop kept in the most impeccable condition by her -justifiably- proud owner. From the moment we set foot on board until the moment we got back on shore at the end of the trip we were completely spoiled – freshly squeezed orange juice in the mimosas, home baked muffins, fresh fruit skewers. When we arrived on Prickly Pear we enjoyed an excellent lunch, snorkeling and basking in the sun. Part of our group had never been sailing and a couple of our number were experienced sailors with experience of traditional boats. Everyone had a great time. Sailing weather was glorious and while the captain certainly didn’t ‘dumb down’ the sailing experience, even the newbies we’re completely comfortable. It was a memorable day and an unforgettable experience.

Visited April 2014

“Highlight of Our Anguilla Visit!”
5 of 5 starsReviewed April 7, 2014

After reading other reviews about Tradition being a must-do in Anguilla, my significant other and I booked a trip and were so glad we did so! It was our first trip to Anguilla and out first full day on the island–a great way to start our trip. We did the day sail to Prickly Pear with the lobster lunch. Another family had booked the same trip as us, but their son came down with the flu and they cancelled, so it turned into a private sail! Laurie, Deb and Brennon crew Tradition and made the experience really special. We had a great time learning about Tradition, hearing stories about Anguilla, spotting sea turtles glide by and relaxing on deck on our sail to Prickly Pear. On arriving at Prickly Pear, we snorkeled for an hour or so. My boyfriend and I thought Prickly Pear was the best snorkeling on Anguilla with Little Bay being the second best (we only snorkeled a few times, so we may have missed good snorkeling elsewhere during our week stay). We had a delicious lobster lunch at the Prickly Pear restaurant beach hut. If you like lobster, this is a must. We found some great shells after lunch on the beach and fed yellow finches sugar right out of our palms. The wind died on our way back to Anguilla so we had to use the motor. In order to not get us back too early since motoring was quicker, Laurie and Deb suggested we go to Little Bay on the way back. We snorkeled here as well and saw huge sea urchins as well as a sea turtle swim ahead of us! Tradition was the highlight of our trip and a truly unique experience. I highly recommend Tradition to all!

Visited April 2014
Ann_2014948from TripAdvisor.comMax Mobilcom
Jim R

“A ‘Must Do’ when visiting Anguilla”
5 of 5 starsReviewed March 23, 2014
We’ve been visiting Anguilla for 15 years and we always try to experience something new each trip. I have to say that this is one of the best experiences yet. Laurie, Deb and Brennon were great hosts (and sailors) and truly added to the great experience with their superb hospitality while providing interesting stories about the island and sailing. My 2 sons (aged 6 and 9) thoroughly enjoyed the day trip out to Prickly Pear. My 9 year has still not stopped talking about having the opportunity to ‘take over the helm’! We’re looking forward to another adventure on Tradition when we return to Anguilla next year.

Visited March 2014

Jim Rfrom


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