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On the Water

Day Cruises

Traditional Sailing Adventure to Anguilla's Prickly Pear Cays

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.
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5.0 73 Reviews
HQ
FREE cancellation

On the Water

Night Kayaking with Liquid Glow

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.
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5.0 3 Reviews
FREE cancellation

On the Water

The Best Sunset Sail and Cocktail Hour in Anguilla

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.
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5.0 39 Reviews
HQ
FREE cancellation

On the Water

Morning Kayaking Tour to Little Bay

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.
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5.0 2 Reviews
FREE cancellation

Sailing

Half-Day Sail, Snorkel Adventure, and Lunch at Little Bay

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. We know nothing gets you hungry like the sea, fresh air and an invigorating swim. Sprawl out in comfort beneath our shady awning while we serve you a scrumptious lunch of Lobster Salad Rolls, Greek Salad, Crisp Cassava Chips, fresh fruit and homemade Tradition cookies. The cooler is fully stocked and there’s always room for a chilled glass of wine, rum punch or an ice-cold beer. After lunch and perhaps another refreshing dip, we’ll get underway and leisurely make our way back home.
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5.0 31 Reviews
HQ
FREE cancellation