City Island is one of New York City’s oddest communities, a sailors’ haven that fancies itself part of New England. “Welcome to New York City’s Nautical Community, 1645,” reads the sign arching over the bridge leading from the mainland. And then you’re there, on a narrow strip of land lined with boatyards, tiny clapboard houses, and bustling seafood restaurants.

Back in the 1700s, the inhabitants of City Island hoped to develop a port that would rival New York’s. Obviously their plan failed, but the community has been home to a number of thriving industries, including a shipbuilding industry that continues to this day. Several America’s Cup yachts were built here.

City Island has only one real street—City Island Avenue. But some of its side roads, which are only a few blocks long, are pretty and worth a gander. To reach the island from Manhattan, take the No. 6 train to Pelham Bay Park, the last stop, and catch the Bx12 (summer only) or Bx29 bus to City Island. This area is perhaps best suited to visit by car to avoid desolate long stretches of waiting for the bus.