The square rigged sailing ships of past centuries relied on the constant airflow from East to West to cruise the Caribbean with amazingly precise schedules. Seamen called this phenomenon the "Trade Winds".

Nowadays, it's the pleasure boater who takes advantage of the reliable winds with the Caribbean considered the best sailing region in the world. Over the past decade, St. Martin has developed into an important yachting center. Conveniently located East of the Virgin Islands and at the beginning of the chain of the Lesser Antilles, St. Martin serves not only as a jumping off port, but as a highly attractive cruising ground in its own right.

The neighboring islands of Anguilla, St. Barths, Saba, Statia, St. Kitts & Nevis and a number of uninhabited islets are only a few hours away by boat. St. Martin itself is the ideal home port for a yacht, as all services to keep a boat afloat and well maintained can be found here. Prices for any imaginable repair or improvement are usually more reasonable than in the US-yachting centers.

Several Charter companies maintain their base on the island. Yachts of different sizes and configurations can be chartered by day or week, to the qualified skipper as a "Bare Boat", and to the beginner or non-sailor with a competent crew.

During a week long cruise many different anchorages can be explored through relatively short hops. Outside the famous Simpson Bay Lagoon, St. Martin features many sheltered bays. Marigot Bay is a comfortable overnight anchorage under most weather conditions and Friars Bay provides a picture perfect tropical backdrop. Grand Case lures with its great selection of restaurants, and Pinel Island is another spot of breathtaking tropical beauty. Orient Bay is well protected for enjoying the beach action and Oyster Pond boasts the best jumping off point for the neighboring island of St. Barths.

On the South Coast, Great Bay with the town of Philipsburg and Simpson Bay (outside the Lagoon) provides adequate protection, but can have somewhat 'rolling' waters.

The itinerary of an easygoing week-long charter could include visits to Anguilla, a British territory and French St. Barths, the famous jet-set spot. Several yachting companies have main offices in St. Martin/St. Maarten and although the trade winds make the traditional Sailing Yacht highly sought after, Motor Sailors, fast Planing Motor Yachts and Displacement Motor Yachts can easily be chartered.