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, sightsee, and sample gourmet fare in upscale restaurants. 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
Day 1: Marigot Bay
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. Snug up behind one of the two cays guarding the entrance to enjoy lunch. 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 (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.
Mooring: No moorings are available. The anchorage is south of Marina Fort St. Louis. There's plenty of space and the holding is good.
Dinghy dockage: Dinghy dockage is available.
Things to do: Restaurants and shopping are the main attractions in Marigot.
Facilities: Dockage, fuel, water, showers, ice, laundry facilities, provisions, Internet access, banks, taxis, and car rentals are available.
Day 2: Road Bay
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.
Mooring: No moorings are available in Road Bay. Moorings are placed throughout the marine park and are available as part of the cruising permit fee on a first come, first served basis. In Road Bay, there is ample room to anchor, except near the ship dock (keep clear of it). Holding is good.
Dinghy dockage: Dinghy dockage is available.
Things to do: Enjoy a meal at one of the restaurants and bars. Johnno's has live music on weekends. The island is large, with small hamlets and all kinds of interesting shops and restaurants spread out along quiet roads. The main settlement is The Valley. Fantastic beaches are everywhere. Consider renting a car to take an island tour. The bird watching is excellent at Caul's Pond. Of course, dive excursions to the reefs are available, if you want a guided tour to some of the best spots, including the seven wrecks sunk on the reef to create a habitat for the myriad tropical fish, sea fans, and corals. Anguilla is sometimes known as the wreck dive capital of the Leeward Islands.
Facilities: Provisions, propane, taxicabs, car rentals, and Internet access are available.
Day 3: Crocus Bay
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.
Mooring: Moorings are available in Little Bay during the day, but not for overnight stays. The anchorage in Crocus Bay is south of Pelican Point. Holding is good.
Dinghy dockage: No dinghy dockage is available. Beach the dinghy.
Things to do: The snorkeling is superb off Pelican Point in Crocus Bay and the beach is excellent for swimming and sunbathing. Just north is Little Bay, which has day-use moorings. The colorful 70-foot cliffs are truly splendid and the birds (including lots of pelicans) are plentiful and fun to watch. The main settlement on Anguilla, The Valley, is within walking distance of the beach at Crocus Bay. The Savannah art gallery, which you'll pass on the way, has a selection of beautiful paintings to admire (or buy). Next to the gallery is Koal Keel, an upscale restaurant and a good choice for dining ashore.
Day 4: Orient Bay
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, where you may have stopped for lunch on the first day of your St. Martin 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.
Mooring: No moorings are available. Orient Bay is wide open to the east. However, there are two good anchorages. The small anchorage on the west side of Ile Pinel is snug and quiet at night, far from the hustle to the south at Green Cay. Holding is good. At Green Cay, the anchorage is also on the west side. Holding is good.
Dinghy dockage: Dinghy dockage is available at Ile Pinel and Green Cay.
Things to do: Ile Pinel is mostly secluded, though there are beachside shacks where you can rent sailboards and other watersports equipment. Snacks and soft drinks are available, and you can arrange a ride in an ultralight aircraft for some incredible, and heart-racing, views. There are also a few restaurants and shops within walking distance of the dinghy docks. On Green Cay, nude sunbathing is popular on the eastern stretch of Orient Beach; elsewhere, swimsuits are more in vogue. Sailboarding and other watersports are popular. Rentals are available. A number of restaurants are on the waterfront and provide a good place to enjoy a convivial atmosphere.
Facilities: Ice is available.
Day 5: Gustavia
Orient Bay to Gustavia - 15 nm. Once you're off Orient Bay, head 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. You can pick up a mooring for free while you visit. Sailors are welcome to come ashore for a quiet stroll. The fashionable and picturesque waterfront town of Gustavia is less than two hours away.
Mooring: Moorings are available for a fee. The anchorage is extensive and often crowded at the peak of the winter season. The bottom is weedy in some places. Make certain your anchor is well set.
Dinghy dockage: Dinghy dockage is available.
Things to do: The boutiques and restaurants are the main attraction of Gustavia, apart from its picturesque town and wonderful French culture. A hike up the hills to the lighthouse at Fort Gustav is worth it for the views. You can also climb the steps up Fort Karl.
Facilities: Water, ice, showers, garbage disposal, provisions, taxicabs, car rentals, and Internet access are available.
Day 6: Anse de Colombier
Anse de Colombier 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.
Mooring: Moorings are available at no charge. There is plenty of room to anchor. Holding is good in sand.
Dinghy dockage: No dinghy dockage is available. Beach the dinghy.
Things to do: Snorkeling is popular in the bay and is good most everywhere. In calm conditions, the rocks surrounding Ile de la Pointe, which hems in the bay to the south, are a great place for snorkeling and scuba diving. South of that Is an islet where sea turtles and sea rays are sometimes observed. At the north end of the beach, you'll find stairs leading to the top of the hills and a scenic trail that meanders through patches of fragrant lilies and cactuses. There are a few shops in the village.
Day 7: Great 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, excellent restaurants, and bustling casinos. There's a beach boardwalk lined with restaurants, well worth a stroll before deciding where to eat dinner.
Mooring: No moorings are available. Anchor off the breakwaters of the inner harbor and north of the cruise ship docks. Holding is good.
Dinghy dockage: Dinghy dockage is available.
Things to do: The shops, restaurants, and casinos are the main attractions of Philipsburg. There is a small museum as well.
Facilities: Dockage, fuel, water, showers, ice, laundry facilities, provisions, Internet access, banks, taxicabs, and car rentals are available.
