The only way on or off Shelter Island is by ferry. There are two ferries connecting the island to both the North and South forks of Long Island and both ferries accommodate passengers and vehicles. The North Ferry is a short five minute walk from the hotel and connects to Greenport on the North Fork of Long Island. The South Ferry is a short 8 minute drive from the hotel and connects to Sag Harbor on the South Fork of Long Island. Both ferries run throughout the day but are first come first serve so be prepared to wait during peak travel periods.
Both the South or North Ferries to Shelter Island can be reached by car in approximately 2.5 to 3 hours from New York City (expect longer on peak summer travel days).
The Hampton Jitney is a luxury coach service that operates out of New York City. Take the North Fork Line from multiple pick up points in Manhattan to Greenport, Long Island. The bus drops off at the North Ferry and once on Shelter Island, The Chequit is a short 5 minute walk from the ferry.
Long Island Railroad offers train service from New York City to Greenport, Long Island, the station is across the street from the North Ferry and once on Shelter Island, The Chequit is a short 5 minute walk from the ferry.
The Long Island Railroad can be easily accessed from JFK airport via the AirTrain which connects every terminal with the Jamaica station. Once at Jamaica you can board a Long Island Railroad train to Greenport, Long Island and connect to the North Ferry (see above).
If you are traveling from points north (Boston, Rhode Island, Cape Cod etc.) you can take the Cross Sound Ferry from New London, Connecticut to Orient Point, Long Island. From Orient Point it is a 30 minute drive to Greenport and the North Ferry to Shelter Island.