Sailing Off the Big Apple

By the early twentieth century, City Island had built a worldwide reputation for building quality wooden boats, especially yachts. Situated in the waters of western Long Island Sound and Eastchester Bay, the island is suitably positioned for great sailing. City Island provided service for schooners stopping along the East Coast, and the yards hired skilled craftsmen to build yachts that would win and defend several America’s Cup races. The Bx29 City Island bus turns around near the southern tip of the island. For a time, the boatyards dominated the economy on City Island, and when the wars came, the boatyards contributed to advances in naval technology, including the World War II era minesweepers. Kids on City Island grew up with the water, catching crabs and rowing small boats. Memories of the glory days of yacht building on a City Island storefront.  City Island built enormous yachts for the Gilded Age robber barons of New York. The island’s most famous contributio...

Sailing Off the Big Apple explores New York City by water, discovering and rediscovering the city’s historic waterways, shoreline developments, and rich maritime culture. Where its sister site Walking Off the Big Apple strolls the streets on foot, this site wanders down to the shoreline and gets on a boat. A motorboat and a sailboat pass like ships in the night during sunny daylight in the East River.  At first, we’ll mostly travel by ferry. The city’s expanding and affordable ferry service is increasingly opening new ways to experience New York City both for residents and visitors. Riding the ferry is a great way to keep up with the transformation of the waterfront and explore unfamiliar neighborhoods. View of Midtown East from the NYC Ferry Over the past few years, many of the city’s old working piers and industrial waterfronts have been repurposed for recreational purposes, transformed into new parks and spaces for entertainment. Where once dockworkers a...