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.

 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.

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

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

There's a reason why locals call St. Maarten "The Night Life Capital of The Caribbean'. Tour the gorgeous island paradise at night with our Local Island guide Sunita, who has picked her favorite Night life Hot Spots on St Maarten. Discover the best Bars, Restaurants, Casinos and Lounges on St Maarten. During this guided Night Life Tour, climb aboard our Air Condition Bus with a dynamic, entertaining guide who will show you the best of St Maarten at Night. 

Best Of St Maarten Private Nightlife 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

Enjoy a 4hours city tour in St Maarten!
Grab your cameras and sunglasses and get ready to visit the beautiful beach of Grand case and get to know the island thru a local.
Book with us today!

City Tour Of St Maarten St Martin 

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

We are the number 1 company in transport services, with the most modern and luxurious fleet. 

We will be able to pick you up where you request it. Please give full details at the time of booking.

Luxury Transport in 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.

The premier provider of executive chauffeured transportation on Anguilla. 

Comfort One Way or Round-trip Transfer from Sint Maarten Princess Juliana Airport (SXM) to hotels or ferry or return.

All Vehicles fully licensed and insured. Our cars are equipped with all necessary facilities for a trip to any part of the world under any weather conditions, including additional fastenings for sports and other equipment.

On your request, we have child seats for all ages. Vehicles are clean inside and outside; our drivers’ always are well dressed and always pay attention to our guests. They speak English. They will meet you with a name sign and help with your luggage.

Experiences in Shoal Bay Village, Anguilla