Shelter Island is a small island 90 miles from Manhattan on the Eastern end of Long Island. It is ONLY accessible by ferry from either the North or South forks of Long Island.
You may take the South Ferry from Sag Harbor, or the North Ferry from Greenport. Reservations for the ferry are not necessary as the ferry runs every 10-15 minutes to the island. You will buy a one-way ticket for about $15, CASH ONLY.
The North Ferry runs between Greenport, NY and Shelter Island. In the fall, the last boat to Greenport is at 11:45pm.
The South Ferry runs between North Haven, NY and Shelter Island. In the fall, the last boat to North Haven is at 12:00am. http://www.southferry.com
We recommend finding accommodations on the island so you don't have to worry about catching the ferry back to either the North Fork or the South Fork at the end of the night.
With our wedding being on a holiday weekend, most hotels and B&Bs require a 3-night minimum. We recommend searching Airbnb, VRBO, etc. as there tends to be more flexibility in the stay minimums.
When searching on Airbnb, be sure to search for "Shelter Island Heights, NY" and/or "Shelter Island, NY". If Shelter Island Airbnbs are booked, search in Greenport, NY.
Shelter Island House features a restaurant, free bikes, a seasonal outdoor swimming pool and bar and is located 10 minutes from Ram's Head Inn. 3-night minimum.
This is the sister hotel to Shelter Island House, just a block away. Guests are welcome to use all the amenities available at Shelter Island House, like the pool, for example. 3-night minimum.
The Chequit was recently sold to new owners. They are aiming to open summer 2021, so they might have rooms open by October.
Dering Harbor Inn just started taking reservations for summer/fall 2021. Please contact them directly for unit availability and pricing as they currently aren't taking online reservations.