Built in 1978, for sail-trading throughout the Caribbean, Tradition has exchanged sailing cargo and contraband for cruising with charter guests and cocktails in Anguilla. This authentic and traditional sailing experience is a must do on your Anguilla itinerary. Sail in rustic luxury, while sipping Mimosas or hand-squeezed orange juice, to one of the jewels in Anguilla’s Marine Park System, the Prickly Pear Cays. Immerse yourself in the stunning reef snorkelling, a delicious Caribbean barbecue on the beach, and Pina coladas at the tiki beach bar. Enjoy the white sand beaches, explore the nesting grounds of sea birds, and hand-feed the bananaquit birds before re-boarding Tradition around 1:30 pm. It's an adventurous and exhilarating upwind sail back to Road Bay and Sandy Ground, a day made complete with rum punch, Tradition's chocolate chip cookies and fresh watermelon. Tradition hosts a maximum of 12 guests and space is limited to a maximum of 12 guests on this 6 hour sail.

Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

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.

The Best Sunset Sail and Cocktail Hour in Anguilla

Indulge in an authentic sailing experience on a classic Caribbean "Rum Runner" of yesteryear as Tradition sails to one of Anguilla's hidden treasures, Little Bay. 

Home to turtles, nesting pelicans, tropic birds and magnificent cliffs, Little Bay is a stunning oasis and a “must do” on your Anguilla itinerary. Dive off the side of Tradition and feast your eyes on a panorama of spectacular marine life as you snorkel through the warm, buoyant waters of the Caribbean.


Little Bay Half-Day Sail & Snorkel Adventure

This will be one of the best tours you did in your life. 4 amazing stops in 4 hours, you will get time to hang out at the main attractions and see all the highlights of the island. This tour is most popular for people who don't want to stay long at a beach. Relax and enjoy the ride as the guide takes you around the island while you sip on some free beverages or try our local rum punch while the guide gives you the island history.

St. Maarten 4 Hour Sightseeing Tour

Night kayaking is a rare and exhilarating opportunity that allows you to explore the waters in a different light. When it comes to kayaking in Anguilla, the experience becomes even more special and unique.

The island of Anguilla boasts some of the most pristine waters in the Caribbean, which makes for perfect kayaking conditions. As you paddle through the dark waters, you’ll be surrounded by the gentle glow of phosphorescence, which will illuminate your path, adding an extra layer of magic to the experience.


Night Kayaking with Liquid Glow

Our morning kayak tour is the perfect way to start your day in Anguilla. Join us as we set out from Crocus Bay and paddle through the crystal clear waters, heading towards Little Bay. Along the way, you’ll have the chance to see a variety of marine life including turtles, stingrays and hundreds of tropical fishes. As we paddle, you’ll be able to take in the natural beauty of the island, viewing caves and cactus growing on the cliff side, and observing sea birds and other wildlife.

We’ll also offer an exciting opportunity to climb a cliff using a rope and then take a dip into the crystal clear waters of Anguilla. Once we arrive at Little Bay, we’ll take a break on a secluded beach and give you the chance to snorkel around the reefs and fully immerse yourself in the crystal-clear waters.

This tour is sure to be an unforgettable experience filled with adventure, nature, and fun.

Morning Kayaking Tour to Little Bay

Discover the vibrant charm of St. Maarten on our 4-hour island tour tour! Immerse yourself in the island's beauty as you explore the pristine shores of Maho Beach while on this true tropical paradise. With a local guide by your side, you'll uncover hidden gems and gain insider insights into the island’s culture and history. Don't miss out on this unforgettable adventure!

Island Experience Of St Maarten St Martin 

Reliable and convenient transportation to and from the Pickup location. Our professional drivers ensure a smooth journey, providing a stress-free experience for travelers. On-time pickups and drop-offs, comfortable vehicles, and excellent customer service make our airport transfer service the perfect choice for your travel needs. Available 24/7.

- 24/7 customer service provides escort for your travel.
- Air conditioned vehicle provides you with a suitable temperature in your journey.
- Professional drivers will take you to your destination directly while avoiding traffic jams.
- Customized services bring you more unique experiences.

Clayton J. Lloyd Airport (AXA) Private Transfer to Anguilla

Our immaculately presented staff are the only certified chauffeurs on Anguilla, with training and certification provided by Pax Training, the gold standard in the industry.

We offer personal travel services based on your needs and your guests’ needs, including security detail, Airport/Seaport Concierge and flight monitoring for delays. The amenities offered in our fleet of late-model vehicles include complimentary Wi-Fi, Bottled Water, Magazines and Mobile Phone chargers.

Experiences in Merrywing Bay, Anguilla