Caribbean verve and European charm commingle in a rare blend of elegant and low-key, laid back Caribbean vibe. Short but invigorating sails take you to some of the best, tranquil, white sandy beaches in the Caribbean. With over 90 beaches between the three islands, each distinctly different from the other, walk into a kaleidoscope of blues that soothe the winter weary.

A St. Martin sailing itinerary has many possibilities. You could spend a week exploring the northern Leeward Islands and sail no more than 21 nautical miles in one day, enjoying leisurely sails and sojourns ashore to shop and sightsee. You could also lengthen the sailing range to include a mix of long and short passages, giving you the opportunity to experience cruising farther south to the picturesque islands of St. Kitts, Nevis, and Antigua. Combining open-water, down-island romps in fair winds with pleasant days of island-hopping a short distance to swim, snorkel, and relax in secluded anchorages is just one of many delights when sailing the Leeward Islands.



Oyster Pond to Marigot – 11 nm. As you make your way northward along the east shore of French St. Martin, you’ll see Orient Bay to port. Just a little farther north is the small island of Tintamarre, another nice anchorage for lunch, depending on the wind direction. Both have fabulous beaches. As you round the top of St. Martin and proceed down the west coast, Grand Case bay will be to port. Usually a pleasant anchorage for the night, it’s known for its wide selection of good restaurants and lively bars. It’s also home to Creole Rock, where the snorkeling is superb. If you wish to go farther west, visit the bustling port of Marigot.


Marigot to Road Bay – 12 nm. Leaving St. Martin in your wake, your course will take you westward to the south end of Anguilla, a low island renowned for its scuba diving, restaurants, and laid-back Caribbean charm. Road Bay is an excellent anchorage, one of the most pleasant in the northern Leeward Islands. It’s also the port of entry for cruising yachts and a great place to go ashore and explore the island. Not far away is 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.


Road Bay to Crocus Bay – 10 nm. It’s about 5 nautical miles from Road Bay out to Prickly Pear Cays, part of Anguilla’s marine park. These tiny islands are a good lunch stop in settled weather for a swim or snorkeling on the reef. Seabirds nest in the craggy cliffs, a pristine white-sand beach fringes the cay, and the colors of the ocean are dazzling. Dnghy ashore to the north side of the island, enjoy a stroll, and listen to the “whistling rocks” as they seem to sigh with the rhythmic wash of the gentle waves. Another five nautical miles back to the main island will take you to scenic Crocus Bay, just north of Road Bay, where you anchor for the night.


Crocus Bay to Orient Bay – 21 nm. From Anguilla’s Crocus Bay, you’ll set a course to take you along the north coast of the island on a downwind sail, until you head up once you’re past Blowing Rocks for the sail east to St. Martin. Your destination is Orient Bay. There are two good anchorages, shoreside attractions, and plenty of watersports to pass the time in true Caribbean style.


Orient Bay to Gustavia – 15 nm. Once you’re off Orient Bay, you will head southward from St. Martin to one of the prettiest locales in the northern Leewards, St. Barths, which is officially known as St. Barthemey. On the way, stop for lunch and some snorkeling at the privately owned Ile Fourchue, a small, hilly isle off the coast of St. Barths. Sailors are welcome to come ashore for a quiet stroll. The fashionable and picturesque waterfront town of Gustavia is less than two hours away.


Anse de Colombier Gustavia to Anse de Colombier – 5 nm. A fast downwind sail takes you northwest along the coast of St. Barths to picture-perfect Anse de Colombier at the very tip of the island. Steep hills overlook the blue waters of the bay. A village is situated nearby and is well worth the hike, in part because on the way you’ll see stunning views of the surrounding islands. Snorkeling, swimming, sunbathing, and relaxation draw sailors to the bay.


Anse de Colombier to Great Bay – 9 nm. Another downwind sail to the northwest puts you in Great Bay on Dutch St. Maarten in a couple hours at most. Philipsburg, the Dutch capital, is a thriving waterfront port with lively nightlife, many interesting shops and bustling casinos.