House Or Rental
As an alternative to the Chequit, we recommend exploring Airbnb / VRBO / similar sites and as there are many options on the island and can be a bit more price-friendly if staying with a group! In addition to the home rentals, there are many smaller bed and breakfasts located around the island and across the way in Greenport. Some of our favorites include the House on Chase Creek, Seven, West Neck Guest House, American Beech, Cliffside Resort Condominiums, and Harbor Front Inn.
Hotel
The Chequit room block is finally up and running, you can book via the website with the below code, or can call the hotel directly. Code: b907764
Discount Code - b907764
Travel Note
Shelter Island and Ram’s Head Inn is most easily accessible via ferry from Greenport, on the North Fork of Long Island. The ferry runs continuously (a boat arrives every 10 minutes) from the hours of 5:15am to 12:45am. The ride is at most 10 minutes from one side to the other. The boat is primarily designed for cars, so it is very easy to bring a vehicle onto the island, but there is plenty of space for people to walk on as well. One-way fares are CASH ONLY and start at $16 for vehicles and $3 for walk-ons. You do not need to make a reservation in advance; it is first come, first served.
Travel Note
For those staying on Shelter Island, we recommend bringing a car, as it is the most effective way to get around the island. Additionally, the Shelter Island Taxi service can assist with any other trips needed around the island.
Shuttle
August 15, 2026 4:30 pm - 10:30 pm
We will provide a shuttle service from the Chequit Hotel to the reception at Ram’s Head at 4:15 and 4:30, approximately. Following the reception at Ram’s Head Inn, there will be a shuttle service to both the Chequit and the ferry.
Travel Note
If you are flying in for our wedding, first off thank you! Renting a car / car pooling with another guest is likely the easiest way to make it from the airport to Shelter Island. Alternatively, if you are flying into JFK, you are able to take public transportation all the way out to Greenport via the Air Train and the Long Island Railroad, and drop off is right in front of the ferry to Shelter Island!
Travel Note
If you are driving down from New England, you may have realized it is quite a drive to traverse Connecticut and then double back across all of Long Island... Luckily for you, the Cross Island Ferry connects New London, CT, and Orient Point at the very east end of Long Island. This can save easily 4+ hours of drive time and offers some great light house views! Once off the boat at Orient Point, it is a short 15 minute drive to Greenport and the ferry to Shelter Island. If interested in bringing your car onto the Cross Island Ferry, we recommend purchasing your ticket well in advance to secure your spot.