The Windward and Leeward islands form the eastern border of the Caribbean Sea. Stretching from Grenada to Martinique, the Windwards got their name because British ships sailing from other colonies frequently had to beat to weather to reach them. The northern islands of the archipelago are more to leeward, so the British called them the Leeward Islands.
St. Martin yachting itineraries have 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 passages with a personable and highly professional captain as your guide. Sojourns ashore to shop, sightsee, and sample gourmet fare in upscale restaurants is part of the magic of crewed St. Martin yachting, as is the wonderful attention and cuisine provided by your private chef. 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 (see St. Martin sailing maps). 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 in the Leeward Islands.
Meals at any restaurant mentioned in this itinerary are not included in the charter price.
Oyster Pond to Marigot – 11 nm. As your graceful luxury yacht makes its way northward along the east shore of French St. Martin, you’ll see Orient Bay to port. Snug up behind one of the two cays guarding the entrance to enjoy lunch prepared by your accomplished gourmet chef. Just a little farther north is the small island of Tintamarre, another nice anchorage for lunch. 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 (dinghy dockage is available). 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, where you can anchor or get a slip for the night.
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 for dinner. 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. Anchor off the south side of East Prickly Pear at the west end of the cay. Seabirds nest in the craggy cliffs, a pristine white-sand beach fringes the cay, and the colors of the ocean are dazzling. Take the dinghy 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 can anchor for the night.
Crocus Bay to Orient Bay – 21 nm. From Anguilla’s Crocus Bay, your captain will set a course to take you along the north coast of the island on a fabulous downwind sail. Try your hand at the helm. Your captain will gladly assist you. You head up closer to the wind once you’re past Blowing Rocks for the sail east to St. Martin. Your destination is Orient Bay, where you may have stopped for lunch on the first day of your St. Martin yachting itinerary. It’s certainly worth a longer stop. 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, your captain will set a course southward from St. Martin to one of the prettiest locales in the northern Leewards, St. Barts, 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. Barts. Moorings are free of charge while you visit. You are welcome to come ashore for a quiet stroll. The fashionable and picturesque waterfront town of Gustavia is less than two hours away.
Gustavia to Anse de Colombier – 5 nm. A fast downwind sail takes you northwest along the coast of St. Barts 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.
Final Morning
Great Bay to Oyster Pond – 4 nm. Although you won’t want to sail back to reality (you can always come visit St. Martin again!), the final leg of your crewed St. Martin yachting adventure will be an easy passage back to the Moorings base. You will arrive by noon.
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