Written by Donna Bowden
July 2019

The well-protected harbor at Greenport has drawn vessels for centuries. Once a whaling and shipbuilding port, it later became a menhaden fishery and oyster center and eventually offered a haven for tourists. Today, visitors come by land and sea with loyal boaters flocking to this destination during the summer months.

Claudio’s, a waterfront landmark, is an eatery established in 1854 by ship worker Manuel Claudio. A magnet for boaters and a bootlegging stop during Prohibition, the restaurant is a popular East End destination. Preston’s Chandlery, a mariner’s browsing treat that dates back to the late 1800s, is another village institution.

For a deep dive into Greenport’s seafaring past, visit the East End Seaport Maritime Museum at the ferry dock. The museum scoots visitors out to the iconic Long Beach Bar “Bug” Light and stages the Greenport Maritime Festival in September. In Mitchell Park, an antique 36-horse carousel makes daily rounds, and the Railroad Museum of Long Island tracks Greenport’s history as the eastern terminus of the Long Island Rail Road.

You can easily branch out from here to Gunkhole in Peconic Bay estuary. Visit a Long Island winery, tee off at a golf course, or take a short jaunt to Shelter Island on the ferry. Dering Harbor and Coecles Harbor have facilities at Shelter Island for transient boaters.


Mitchell Park Marina


Located in the center of the village, transient boaters are accommodated at the 60-slip town marina and 220-feet plus yachts dock at a 640-foot standing pier.

Greenport Yacht Yard


This is one of two Safe Harbor marinas on the east side of Stirling Basin. It offers more than 200 slips and many amenities, including courtesy transportation to town.

Stirling Harbor Marina


This Safe Harbor marina inside Stirling Basin has 185 slips and takes vessels up to 90 feet. A restaurant is on-site, along with a complimentary shuttle into the nearby village.


The Frisky Oyster


A fine-dining atmosphere in the village offers a creative dinner menu that is updated daily.

Brix & Rye on Main Street


Highly rated pizza with a make-your-own option is served alongside classic cocktails in a speakeasy atmosphere.

Claudio’s Restaurant


This seasonal East End eatery has
a long history of being a lively destination with fresh seafood and live music on weekends. Also on-site are a clam bar and crab shack.



This year-round restaurant serves seasonal dishes with regional fare and uses innovative recipes for classics and small plates. Long Island wines are available.

Porto Bello Restaurant & Bar


Enjoy fine Italian dining on the waterfront at Stirling Harbor Marina.