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This area of the Caribbean offers many possibilities for cruising. You could sail up to 21 nautical miles a day and discover exceptional spots for eating, shopping and sightseeing. The best beaches on the island are found across the French and Dutch sides, featuring excellent spots for fishing, snorkeling and diving. You could cruise through the open waters and spend your days island-hopping and exploring hidden gem anchorages.
We have a host of recommendations for this trip. With so many treasures to discover on land and sea, this itinerary covers favorites including Marigot, Orient Bay, Gustavia, Anse de Colombier, Great Bay, Philipsburg, Road Bay, and Crocus Bay and stops in St. Barts and Anguilla.
Marigot is the capital of the French side of St. Martin. The waterfront is attractive, shops and boutiques are plentiful, and restaurants are known for quality French cuisine. Casual eateries also abound, as do fun bars with live entertainment.
The island of St. Martin has two spellings, because half of it is French (St. Martin) and the other half is Dutch (St. Maarten). More than 1 million visitors arrive every year to enjoy duty-free retail, idyllic beaches, luxury hotels and casinos.
The annual St. Maarten Heineken Regatta in March and Classic Yacht Regatta in January are major events. Full-service marinas in Simpson Bay and Simpson Bay Lagoon always bustle with activity, and superyachts are everywhere. Marine parks on the island offer superb swimming, diving and snorkeling.
On the northwest coast along the Anguilla Channel lies Grand Case, a showpiece destination with a 1.6 km-long beach overlooking a turquoise lagoon. Relax in a lounge chair with a cocktail, snorkel among colorful fish or gaze at breath-taking sunsets. Gourmet restaurants and bars along the main street serve delicacies featuring cuisines from around the globe.
Where to Dock: Marina Fort-Louis
Estimated Mileage: 9 – 10 NM
On the northeast coast, yachting in Orient Bay is popular among boaters cruising the northern Leeward Islands. Aside from its white-sand beach, plethora of watersports, kite surfing, windsurfing and kayaking, and many restaurants and boutiques, the bay has a quiet side as well. A lively nightlife attracts many guests, but a relaxing evening aboard in a scenic anchorage is also a favorite pastime. The only caveat is that Orient Bay can be difficult to enter in certain conditions, so careful attention is warranted.
Îlet Pinel is mostly secluded, but you find beachside shacks to rent windsurfing and other watersports equipment. Snacks and sodas are available, and a few restaurants and shops are in walking distance of the dinghy docks. On Green Cay, nude sunbathing is popular on the eastern stretch of Orient Beach; elsewhere, swimsuits are in vogue.
About 2 miles northeast of St. Martin is a tiny uninhabited island called Tintamarre that’s a day tripper’s delight. It once served as a cotton plantation and small local airline, but the 250-acres of land is now part of the Nature Reserve. Bring your own provisions and snorkel gear, because no restaurants or shops are on-site. Instead, visitors find one gorgeous beach with a shipwreck offshore and another with a lagoon and coral reef that’s teeming with aquatic life. Coastal cliffs add to its untouched beauty.
Where to Dock: Anse Marcel Marina
Estimated Mileage: 25 NM
The main port of entry on St. Barts is the scenic and chic harbor of Gustavia, tucked away on the south side of the island. Snug and protected, this harbor attracts wealthy superyacht owners. Boutiques displaying famous designer wear and jewelry vie for space with restaurants specializing in French cuisine, though casual dining places also line the picturesque streets.
The red roofs of many buildings give Gustavia a distinct character. Some call it the “Riviera of the Caribbean.” A hike up the hills to the lighthouse at Fort Gustav is well worth it for the views of the surrounding islands or climb the steps up Fort Karl for more exceptional scenery.
St. Barts (St. Barthélemy) is a relatively small island popular for the French allure of Gustavia. A mix of boutiques, art galleries and fine dining attract visitors at the base of lush green hills. The quiet, charming anchorage at Anse de Colombier is off the beaten track, promising a restful night in an exquisite setting. The pristine beach curves along the shore, perfect for swimming and sunbathing, snorkeling and scuba diving.
Where to Dock: Port de Gustavia Marina
Estimated Mileage: 4 – 5 NM
Scenic and well protected, this horse- shoe-shaped bay at St. Barts’ western tip is popular among cruisers for its beauty, beach and snorkeling. Steep hills overlook blue waters, where you discover a multi- tude of yachts at anchor. On the southern hill sits a house built by the Rockefeller family, who once owned Anse de Colom- bier. Now, it’s part of the St. Barts Marine Reserve. Its bay has no road access, but a trail leads up the hills to the village of Anse de Flamands.
Snorkeling is good all around the bay. In calm conditions, the rocks surrounding Île Petit Jean offer a great place to snorkel and scuba dive. Just south is an inlet that sea turtles and rays call home. At the north end of the beach, stairs lead to the top of the hills and a scenic trail that meanders through patches of fragrant lilies and cactuses. A few shops are in the village.
Where to Dock: Anse de Colombier anchorage
Estimated Mileage: 19 – 20 NM
Philipsburg, capital of Dutch St. Maarten, is a busy place with all the amenities a boater could want. Marinas, a long boardwalk, waterfront restaurants, casinos, watersports and energetic nightlife make Great Bay cruising an adventure on the island.
Tucked between the Great Bay and Great Salt Pond, the town is decked out in vibrant colors and unique architecture from the homes and churches to the iconic courthouse. A quest to learn about the local culture leads guests to the Sint Maarten National Heritage Museum, Fort Amsterdam, art galleries, live music and more.
Where to Dock: Dock Maarten anchorage
Estimated Mileage: About 15 NM
North of St. Martin lies the British island of Anguilla. Road Bay, the main port of entry, offers one of the nicest anchorages in the Northern Leewards. A sugar-sand beach runs along the shore, where casual restaurants and bars await. Laid-back and unpretentious is the rule on Anguilla, one of the chief appeals of yachting here.
During your visit, enjoy the restaurants and bars with lively music. The island is large, with small hamlets and interesting shops and eateries spread out along quiet roads. The main settlement is The Valley, fantastic beaches are everywhere, renting a car for an island tour is easy, and birdwatching is excellent at Cauls Pond. Don’t miss diving excursions to the reefs with guides showing the best spots, including the seven wrecks sunk on the reef to create a habitat for tropical fish and coral. Anguilla is known as the wreck dive capital of the Leeward Islands.
With beautiful beaches, numerous coves and bays, and a marine park, Anguilla is relaxed Caribbean charm at its best. The mix of quiet anchorages and towns with tropical amenities has long attracted boaters. Snorkeling on the reefs among tropical fish is excellent, and scuba diving on the wrecks is some of the best in the Caribbean. Dives off Sandy Island and the Prickly Pear Cays are popular. The anchorage off Crocus Bay, on Anguilla’s north shore, is protected, calm and stunning.
Where to Dock: Road Bay Sandy Ground Village or Rendezvous Bay anchorages
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Estimated Mileage: 19 – 20 NM
Cruising Crocus Bay brings you to a secluded anchorage with colorful 70-foot cliffs rising from sun-kissed beaches. Snorkeling is outstanding from Pelican Point in Crocus Bay, and the beach is ideal for swimming and sunbathing. Just north is Little Bay, which has day use moorings. Birds, including lots of pelicans, are plentiful and fun to watch.
The main settlement on Anguilla is within walking distance of the beach at Crocus Bay. The Savannah Art Gallery, which you pass on the way, has a selection of unique paintings to admire or buy.
Where to Dock: Crocus Bay
ITINERARY PROVIDED BY MOORINGS CHARTERS
The Moorings offers sail and power charters throughout the world including St. Martin in the Caribbean. Visit The Moorings to learn more.
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