Shelter Island Car Service

Shelter Island is a 12-square-mile island sitting in the Peconic Estuary between the North and South Forks of Long Island. With roughly 2,400 year-round residents, no bridges, no traffic lights, and a 2,000-acre nature preserve covering nearly a third of the island, Shelter Island is the Hamptons' quietest and most naturally preserved community. The island is accessible only by two passenger-and-vehicle ferries.

The island is best known for the Mashomack Preserve (a Nature Conservancy property covering roughly 2,039 acres), Sunset Beach (André Balazs's beachfront hotel and restaurant), Ram's Head Inn, and Pridwin Hotel & Cottages (a historic waterfront resort). Summer population roughly triples to 8,000-10,000 with residents arriving at their second homes and day-trippers visiting via the ferries.

Drive times from Shelter Island (ferry crossing + driving): 100 miles and 2 hr 15 min to JFK, 104 miles and 2 hr 30 min to LGA, 30 miles and 40 min to ISP, 115 miles and 2 hr 45 min to Midtown Manhattan. North Ferry to Greenport takes 10 minutes; South Ferry to North Haven (Sag Harbor) takes 10 minutes. The island's main route is Route 114, which runs north-south and connects both ferry docks.

As of 2026, Detailed Drivers serves 67+ cities across the United States. Our Shelter Island clients include second-home owners in Dering Harbor and Shelter Island Heights, Mashomack Preserve donors, Sunset Beach guests, and wedding parties at Ram's Head Inn and Pridwin Hotel. Our chauffeurs are familiar with both ferry schedules, both ferry fare structures, and every venue on the island.