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St. Martin, St. Barths, Anguilla Yacht Charter Itinerary

Adventure to the Cosmopolitan Caribbean with its French, Dutch, British and West Indian Flavors

An exciting St. Martin sailing itinerary that offers a blend of cultures, lifestyles, and landscapes. Made up of several islands operating as different countries, the Leeward Islands stretch 120 miles from Anguilla to Dominica. You’ll find a diverse geography ranging from lush rainforest mountains to flat coral sand islands and giant volcanic craters. You’ll also experience rich history and a variety of nationalities, languages, cultures and cuisines. Several yacht charter itineraries are available in this location. Here is a popular St. Martin sailing itinerary:


  • Day 1 Arrival in St. Martin

    Arrival in St. Martin - one island, yet two countries and two languages. One Dutch, one French and both with a West Indian blend. This island has it all - shopping, golf, casinos, discos, beaches, and stunning scenery.

    Set sail on your own St. Martin sailing charter for Road Bay, Anguilla. This may be the only capital whose main street is a long stretch of powder white beach. Anguilla is laid back island with its own distinct geography and culture. It is a low-lying island edged with pristine beaches and coral reefs teeming with fish. You won't find any cities or major villages here. Instead, there's a sprinkling of cottages and hotels scattered about the island with farm animals roaming freely along the mostly dirt roads. But even outposts have their watering holes, and Road Bay on the North side is often pulsating with calypso and reggae rhythms.

  • Day 2 Prickly Pear Cays and Crocus Bay

    Anguilla is home to some of the best resorts in the Caribbean. You can customize your St. Martin sailing itinerary to sneak ashore for a spa treatment at Cap Jaluca, tee up at the island’s golf course, or arrange a tour of the local art boutiques.

    Or if snorkeling and beaching is your siren’s song, Prickly Pear Cays are a litter of islands off of Anguilla where the preservation of natural beauty is evident. You cannot anchor here overnight as it is a preserve so we’ll head for Crocus Bay – a couple of restaurants but otherwise remote and relaxed.

  • Day 3 Tintamarre and Ile Pinel

    Today, we’ll point the bow of our St. Martin sailing charters in the direction of St. Barths with a lunch stop at Tintamarre - long stretch of sunsplashed beach that melts into turquoise waters... an ancient site of celebration for the Arawak Indians. A short hike will bring you the famous mud baths if your game for a wallow in the mud.

    After lunch, we’ll cast off for Ile Pinel a delightful little island off of St. Martin with a few beach bar restaurants right on the sandy shore. A short hike takes you to a some great vistas.

  • Day 4 Ile Fourche

    Set sail for Ile Fourche, the rugged island moonscape island off of St. Barths and a nature lover's paradise. Ideal for snorkeling and watersports.

  • Day 5 St. Barts

    Anyone who has ever been to St. Barth's agrees - it is captivating and magical. A charming flavor of France in the midst of the Caribbean Sea, only aboard St Barts yacht charters. The scent of croissants in the air, the banter of the French West Indian accents, the smiling faces of the people on the streets, the hint of celebrities on the island... all add to its allure. The main port, Gustavia, rises gently up the hillside from the water's edge with boutiques and fine restaurants throughout. The beaches of the island are superb and never-ending. You might want to rent a jeep and tour the island, grab a beer at Cheeseburgers in Paradise, or saddle up and ride a horse in the countryside. Also great scuba diving is available at St Barts yacht charters.

  • Day 6 Another Day in St. Barts

    Most people want to spend two nights here – the first in Gustavia and the second in Baie de Colombier, a more remote anchorage that offers superb snorkeling and pristine natural beauty.

  • Day 7 Simpson Bay, St. Maarten

    Late afternoon, we’ll return to St. Maarten. Of course, the shoppers may want to return a bit earlier Phillipsburg on the Dutch side is the hub of duty free shopping mecca with dozens of shops selling jewelry, perfume, island handicrafts, souvenirs, linens, and crystal.

    Marigot on the French side has an abundance of boutiques with the latest in European and tropical fashions. The open air market at the harbor bustles with the selling of fresh foods and local crafts. Both Marigot and nearby Grand Anse have sidewalk cafes serving French, Creole and West Indian Cuisine. Or you can saunter down a side street for some roast pig or chicken being barbecued in the open air by some locals.

    Enjoy a relaxing evening on St Martin sailing charters or step it up and roll the dice at the Casino Royale.


  • Day 8 Disembarkation at Noon, St. Maarten

    Remember, this is one of many St. Martin sailing itineraries. Let our knowledgeable yacht charter brokers along with your captain create a personalized itinerary just for you.

Our Expert Opinion

We call this the “Cosmopolitan Caribbean” – a unique blend of cultures and a shoreside ambiance that ranges from barefoot beach bars to upscale, trendy restaurants and resorts. St. Barth’s has an international reputation of a “be there and be seen” island and boasts some dazzling white sand beaches. In the winter time, the seas can be robust so we recommend that you charter a superyacht or a large sailing yacht/catamaran.

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