City Island is New York City’s best-kept secret! City Island is a small island community, 1½ miles long and ½ mile at widest point, at the northeast edge of New York City surrounded by the Long Island Sound and Eastchester Bay. City Island has a rich nautical history. Originally inhabited by the Sinanoy Indians, City Island was established as an English settlement in 1685. The island became an important shipbuilding and yachting center during the 18th and 19th centuries and on through the mid-20th century. It was incorporated as part of New York City in 1896. Today the presence of yacht clubs, sailing schools, marinas, fishing boats and marine supplies and repair shops reflect City Island’s role as a nautical community.