You’ll find there are several lee anchorages when you cruise in Long Island.

There are the usual easterly trade winds along the northern half of Long Island, some with sandy beaches and access to the small villages that dot the main highway running the length of the island.

But south of Deadman’s Cay, you will leave the bank, and the shoreline is much more forbidding, with no good stops for the cruising boats.

Cape Santa Maria marks the northwest end of the island. Just a few miles south of the Cape, Calabash Bay is a popular stopping point for boats arriving from the north. There are several entrances through the protecting reef, then a large area suitable for anchoring with a good sand bottom off a gorgeous beach.

The real attraction here is the Cape Santa Maria Beach Resort, which welcomes visiting cruisers to the excellent restaurant, bar, and store. There is plenty of uncrowded beach to enjoy, and the resort grounds are attractive for walking. But if there is a strong northerly or northeast swell on the Atlantic, it will wrap around the Cape and create an uncomfortable surge in this anchorage. In that case, you will likely want to move farther south.

Cruising Destinations

The common destination for cruising boats is Thompson Bay and the village of Salt Pond along its eastern shore. There are no marinas here, but the anchorage is large and offers good protection in most weather. The town is friendly and provides all the services a cruising boat will generally need. Indian Hole Point wraps the western shore of the bay, and some smaller cays give a bit of protection to the south.

Boats commonly weather a frontal passage here, although the initial southwest wind can make it uncomfortable for a while. But when the breeze shifts to the west then northwest, the water settles down nicely. Many boats will move over to the western shore of the bay early, then back to the eastern side when the wind clocks into the northeast.