The Leeward Islands:
A Sample Itinerary
The Leeward Islands are a sailor's paradise!
The romantic European heritage of the Leeward Islands is unmistakable in this colorful blend of French, English, Dutch, and local culture, all set in a land where rich green volcanic peaks tumble down to sparkling waters and brilliant palm-fringed beaches.
There are more varied experiences here per square mile than anyplace on earth:
• Walk through Marigot and shop the colorful market in the French capital
• Sail to St. Bart’s for sophisticated living and mouth-watering croissants
• Dive Anguilla's reefs, the "Wreck Dive Capital of the Caribbean"
• Sway to the uniquely local island sound of Zouk bands
• Sail northeast to the quiet islands and beaches of Ilet Pinel, Ile Tintamarre
• Ashore, fine restaurants serve the freshest seafood in a variety of styles born of European kitchens and glittering casinos provide excitement around the clock
Day 1 / Night 1
Leave from Simpson Bay for a short sail to Marigot, capital of the French side, for a little shopping at the Creole market!
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The waterfront is attractive, the shops and boutiques plentiful, and the selection of restaurants varied and known for quality French cuisine.
Depart Marigot and escape to the beautiful island of Anguilla (3 hours sail). Sail down to Sandy Island, one of many off-lying areas in Anguilla protected as a marine reserve and a good choice for an afternoon spent swimming or snorkeling Sail back to Crocus Bay for the night. |
This is a peaceful and secluded anchorage with cliffs rising from white-sand beaches. Spend your evening in Crocus Bay, where you can enjoy swimming in the afternoon and a barbecue on your yacht in the evening. The snorkeling is superb from Pelican Point.
Day 2 / Night 2
Sail from Crocus Bay to Prickly Pear for the day, and then sail down to Scrub Island to spend night 2 at anchor (BBQ under the stars on Scrub Island).

Prickly Pear Island Anguilla |
Day 3 / Night 3
From Scrub Island, sail south to Tintamarre through Windward Point. Spend a relaxing day on the beach in Tintamarre. Spend your 3rd night at anchor. Enjoy a mud bath about 100 feet inland.
Day 4 / Night 4
From Tintamarre sail down to St Barth- Gustavia. Visit the island and enjoy some French shopping.
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Snug and protected, this harbor is a favorite among wealthy owners of superyachts. Boutiques featuring world famous designer wear and jewelry vie for space with superb restaurants specializing in French cuisine, though more casual places to dine are also nestled on the picturesque streets.
The red roofs of many of the buildings give Gustavia a distinct character. |
Some sailors call it the Riviera of the Caribbean. Gustavia is a highlight of any Eastern Caribbean yacht charter.
Stay in Gustavia for the day / evening and explore the beautiful Bay St Jean or take the short sail to Colombier, by the Rockfeller mansion. Spend the afternoon snorkeling the point. Enjoy the evening relaxing on board.
Day 5 / Night 5
This day you might spend enjoying all that St Barts has to offer:
10 Exotic Beaches
Many Wonderful Spas
High End Duty Free Shopping
Countless French Restaurants
Night Life St Barts Style
Local Crafts and Jewelry
Endless Watersports including Surfing
Fascinating History
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Day 6 / Night 6
Sail downwind from Colombier to Ile Fourche. Spend the night at anchor.
Day 7 / Night 7
Depart Ile Fourche and sail down to sparkling Orient Bay on St. Martin, one of the loveliest anchorages on the island, with magnificent white beaches and clear turquoise waters.

Orient Bay |
Day 8
Depart Orient Bay back to Simpson Bay. Stop off at Philipsburg, where you'll enjoy duty free shopping. Depart your yacht at noon and transfer to your hotel. If you are flying out that day, the international airport is just minutes away.