North Long Island: Cape Santa Maria to Gray's
In the far north you will find two large resort communities: Cape Santa Maria and Stella Maris. Scattered between are the small settlements of Seymour's, Glinton's, and Burnt Ground. Columbus originally named the island's northern tip Cape Santa Maria after the largest of his three ships. The beach here is gorgeous, full of private homes and resort villas, and a restaurant, bar, and gift shop that are open to the public. North of the Cape Santa Maria Resort are the Columbus Monument, commemorating Columbus's landing on Long Island, and Columbus Cove, where he made landfall. Twelve miles south of the Cape, Stella Maris, which means Star of the Sea, is home to the so-named resort. The Stella Maris airport sits on the property, along with private homes, restaurants and bars, the magnificent Love Beaches, a full-service marina, and a tackle and gift shop; all open to the public. Just north of Stella Maris, off Queen's Highway, are the ruins of the 19th-century Adderley's Plantation.
Traveling south about 8 miles, you'll come to Simms, one of Long Island's oldest settlements. The Tropic of Cancer cuts through the island close to here, dividing the subtropics from the tropics.
Farther south are the idyllic communities of Thompson Bay and Salt Pond; both providing safe harbors for those who visit by sailboat. Salt Pond, a hilly bustling settlement so named for its many salt ponds, hosts the annual Long Island Regatta. Continuing south, you will pass the settlements of the Bight and Gray's before reaching Deadman's Cay.