Pridwin Travel Guide
Planes, trains, automobiles—and a quick ferry ride! Travel to Shelter Island is easy using a variety of transportation methods.
Travel Guide
Whatever your preference, we'll help you plan your trip every step of the way.
Trust us: taking the Ferry to Shelter Island is a breeze. It's a simple ten-minute ride over the sparkling waters of Shelter Island Sound. Plus, no reservations are required, and wait times are usually minimal.
There are two ferries—one at each end of the island—operating in a constant loop daily. The North Ferry departs from Greenport, New York and the South Ferry from North Haven, New York. Traffic is boarded on a first-come, first-serve basis. Cars, bicycles and walk-on guests pay on board.
Please note that tickets for both the North Ferry and the South Ferry are cash only.
Trips can be purchased one way or round trip, depending on guest preference and travel plans. (Tip: For the North Ferry, Greenport offers a quaint and walkable downtown area with shops and eateries. For the South Ferry, Sag Harbor is the home of our sister property Baron's Cove—the perfect Hamptons spot to stop for lunch with a water view.)
To learn more about ferry service to Shelter Island, please visit NorthFerry.com and SouthFerry.com.
The Hampton Jitney is an easy car-free method of travel to Shelter Island from New York City. The Jitney departs from either 83rd Street or 41st Street in Manhattan, and takes you right to the North Ferry Terminal in Greenport. From there, walk on to the North Ferry, and text us at (631) 888-9421—we'll send our Pridwin Chauffeur down to pick you up.
To learn more about the Hampton Jitney, visit HamptonJitney.com.
Departing from New York City's Penn Station, the Long Island Railroad offers an easy 3 hour, 45 minute train ride to Greenport, New York. The route includes one transfer in Ronkonkoma, Long Island.
To learn more about the Long Island Rail Road's service to Greenport, visit LIRR42.MTA.info.
Taking a plane to Shelter Island from New York City is easier than ever thanks to our friends at Tailwind Air.
This incredible seaplane service offers a direct 45-minute flight to Shelter Island from New York City, departing from East 23rd Street in Manhattan, and landing right on the sparkling waters of Crescent Beach. Once you land, our Pridwin boat, Fred's Folly, will bring you to shore. Talk about a memorable travel experience!
Tailwind Air also offers seaplane flights from Boston Harbor, Nantucket Memorial Airport, Bridgeport, Newport, Provincetown, and Plymouth—with more locations in the works.
To learn more about Tailwind Air's seaplane service to Shelter Island, visit FlyTailwind.com.