Leeward Islands – See also: USVI  |  BVI

Experience the flavors of French and Dutch culture when you cruise the Leeward Islands, spanning 200 miles and encompassing 10 major islands. Find hidden coves, stunning white-sand beaches, and quaint village life. Go ashore to enjoy sophisticated nightlife, or relax in tranquil paradise. The choice is yours.


For best results, tell your dates and ideas to our complimentary planning service today.

Leeward Islands Luxury Yacht Charter Itinerary Map

Click to enlarge

Day 1:  Simpson Bay, St. Maarten to Marigot

Leave from Simpson Bay Lagoon in St. Maarten and take a short sail (approximately 2 hours) to Marigot, the capital of the French side of the island, where it is called St. Martin. Reminiscent of a Riviera seaport, Marigot has a lovely waterfront market for shopping and strolling.  Anchor here for your first night.

Day 2: Anguilla 

Depart Marigot and sail (approximately 3 hours) to the lovely island of Anguilla, surrounded by white sand beaches and coral banks. The diving is good here, with as many as 16 good dive sites. Clear customs in Road Bay, the main port of entry, and continue sailing to Sandy Island, a circle of sand with a few baby palms. Spend the night at Crocus Bay, where you may want to do some snorkeling.

Day 3: Prickly Pear Cays

The beautiful underwater canyon near Prickly Pear Cays is home to all kinds of fish, including nurse sharks. Sail to Scrub Island to anchor for the night. Perhaps enjoy a beach barbecue under the stars.

Day 4: Tintamarre

Travel southeast through windward point to Tintamarre, which has a beautiful beach on its western shore and paths suitable for hiking. The water is generally clear, and snorkeling reveals many colorful fish. Anchor here for the night.

Day 5: St. Barts

Sail on to Saint Barthelemay (St. Barts) and clear Customs, then a short sail brings you to Anse de Colombier, a secluded bay set at the bottom of a steep, craggy hill. Colombier was originally owned by the Rockefeller family, who built a mansion on the southern hill. Enjoy the beautiful beach here.

Day 6: Ile Fourchue 

Your destination for today is Ile Fourchue, conveniently located between St. Martin and St. Barts. It’s dry and rocky, and some of the steep hills are a red color that makes for an interesting view.

Day 7:  Return to St. Maarten

Get an early start for your 3-hour sail to Simpson Bay, arriving in time to catch the 9:30 bridge.

Make it happen!  Send your desired dates and itinerary ideas to our complimentary planning service today.

Best time to go: October – April

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