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Join Rusty Pete as we meander our way along the northeast coast of French St. Martin to Orient Bay where you will enjoy a plethora of watersports, kite surfing, windsurfing, kayaking, and many restaurants and boutiques.  The small island of Tintamarre, where we will explore the fabulous bleached white beaches before we head to Anguilla, where you will lay on the beach, soak up the sun with an Island Rum drink and enjoy the breathtaking scenery. The main port of entry on St. Barts is the scenic and chic harbor of Gustavia, situated on the south side of the island near its western end. Boutiques featuring world famous designer wear and jewelry vie for space with superb restaurants specializing in French cuisine, though more casual places to dine are also nestled on the picturesque streets. The red roofs of many of the buildings give Gustavia a distinct character and some sailors call it the Riviera of the Caribbean. 


Contact Captain Rusty Pete for more information at

Road Bay, Anguilla

St Martin from the air

Tintamarre Island, St Martin

Travel Information

Fly to Princess Juliana International Airport (6 km from the base – 15 minutes by car)

Tentative Itinerary

Day 1: Road Bay

Leave from the Marina Fort Louis in 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.

Day 2, 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.

Day 3, 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.

Day 4, 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.

Day 5, 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.


Day 6, Shelly Beach

A short sail over to Shelly Beach where you can spend the day snorkeling, sunbathing or head ashore to shop and explore the town. 

Day 7, Marigot

Anse de Colombier to Marigot Bay. Another downwind sail to the northwest, the final leg of your charter will be an easy passage back to the Charter base. Please check in by noon.

LEEWARD ISLANDS 2021 - $1,895pp (double occupancy)

May 8th - 15th, 2021

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