A St. Martin cruising 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 travels and sojourns ashore to shop, sightsee, and sample gourmet fare in upscale restaurants. You could also lengthen the chartering 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 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 cruising the Leeward Islands.

Please note: Current itinerary options may vary due to government COVID travel regulations in this destination. 

Day 1


Marigot is the capital of the French side of St. Martin. The waterfront is attractive, the shops and boutiques plentiful, and the selection of restaurants varied and known for quality French cuisine. Of course, casual eateries also abound, as do lively bars with live entertainment. Cruising in Marigot is a wonderful way to ease into a St. Martin yacht charter.

Day 2

Orient Bay

Situated on the northeast coast of French St. Martin, yachting in Orient Bay is popular among sailors cruising the northern Leeward Islands. Aside from its beautiful white sandy beach and the plethora of watersports, kite surfing, windsurfing, kayaking, and the many restaurants and boutiques, the bay has a quieter side as well. If you want nude beaches and lively nightlife, it is available, however, a relaxing evening aboard in a scenic anchorage, is also a favourite.  The only caveat is that Orient Bay can be difficult to enter in certain conditions. At all times, careful attention is warranted.

Day 3


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. Snug and protected, this harbor is a favorite among wealthy owners of superyachts. 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. Some sailors call it the Riviera of the Caribbean. Cruising in Gustavia waters is a highlight of any Eastern Caribbean yacht charter.

Day 4

Anse de Colombier

Scenic and well protected, this horseshoe-shaped bay at the western tip of St. Barts is popular among cruisers for its beauty, beach, and snorkeling. Steep hills overlook the blue waters, where you’ll find all manner of yachts at anchor. On the southern hill is a house built by the Rockefeller family, which once owned Anse de Colombier. Now it’s part of the St. Barts Marine Reserve. The bay has no road access, but there’s a trail up the hills to the village of Anse de Flamandes, on a nearby beach. When you go yachting in Anse de Colombier, you’re sure to find the beauty and charm of the Eastern Caribbean.

Day 5

Great Bay, Philipsburg

Located on the shores of Great Bay, Philipsburg, the capital of Dutch St. Maarten, is a busy place with all the amenities a boater could want. Marinas, waterfront stores and restaurants, a selection of casinos, and plenty of nightlife make Great Bay cruising one of the more popular adventures on the island.

Day 6

Road Bay

The main port of entry to the British island of Anguilla, Road Bay, is one of the nicest anchorages in the northern Leewards. A beautiful white sandy beach runs along the shore, where you’ll find numerous casual restaurants and bars. Laid-back and unpretentious is the rule on Anguilla, one of the chief appeals of Road Bay yachting.

Day 7

Crocus Bay


Crocus Bay cruising brings you to a peaceful and secluded anchorage with cliffs rising from white-sand beaches.

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