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I have always thought of Gardiner’s Bay on the east end of Long Island, New York, as special. Native Americans, colonists, pirates and generations of baymen thought so too. Today, recreational boaters agree. I’ve been sailing Gardiner’s Bay for 40 years. Its beauty never fails to inspire awe. The many coves and harbors make for an ideal weekend or weeklong cruising experience as there are superb anchorages and endless things to do ashore.

The bay lies 20 statute miles southwest from New London, Connecticut, and 54 miles southwest of Newport, Rhode Island. To the east is Gardiner’s Island, south is Three Mile Harbor/East Hampton, west is Shelter Island and to the north are the towns of Orient and East Marion. North to south, the Bay spans 10 miles and east to west 8 miles.

If you haven’t cruised here before, know that there are shallow spots, primarily off the Shelter Island shore. However, most of the bay waters are between 20 to 50 feet deep. Coming from the east, the best entry is north of The Ruins and south of Plum Island. If you arrive from points north, be prepared to experience Plum Gut, home to some of the swiftest currents on the East Coast. When there is a strong blow, wind against tide can set up roiling seas. After you make it through, head for the following locations.

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GARDINER’S ISLAND Once in the bay, you can anchor in Cherry Harbor on the west side of Gardiner’s Island. There, except for two old houses and a windmill, you’ll see an original British land grant, almost untouched for centuries. The 3,300-acre parcel has been privately owned by the Gardiner family since 1639. As it is prohibited to go ashore here, even below the mean high tide line, your boat will be monitored by onshore security.

If the wind is out of the southwest, head to the other side of the island and anchor in Tobaccolot Bay, just south of Eastern Plain Point. You will probably be alone. Use the time to reflect on the amazing birdlife and the pristine vegetation ashore. History buffs should note the high ground has concrete pillboxes once used to spot German submarines.

The southern channel is easily done in a powerboat, but it requires heads-up navigation in a sailboat as it winds like a serpent around several sandbars. Every year I circumnavigate the island solo under sail; it takes me about 4 hours.

THE HAMPTONS If you’re in search of an eclectic collection of tony restaurants, serious shopping for clothes and jewelry, or cultural enrichment at places like the Parish Art Museum in Water Mill, head into Three Mile Harbor. Its narrow but easy-to-navigate channel leads to a large anchorage. Once in, you are protected on all sides, so you’ll get a good night’s sleep. There are several marinas on the eastern shore that have dockage, fuel and services, as well as land access. Once ashore you will need to call a car service to get to the towns of Amagansett, East Hampton, Bridgehampton or Montauk.

If you leave Gardiner’s Bay and head southwest into Northwest Harbor, it is possible to anchor or moor right off the lively old whaling town of Sag Harbor and walk to everything. As you’ll learn at the Whaling and History
Museum, this town was once one of the largest ports in America. A short walk past Main Street shops into the residential area brings you to scores of historic houses lining the leafy streets.

The charming old whaling town of Sag Harbor, New York, was once one of the largest ports in the U.S.

The charming old whaling town of Sag Harbor, New York, was once one of the largest ports in the U.S.

SHELTER ISLAND Heading due west lies Shelter Island, with several bays and harbors to explore. The entrance to Coecles Harbor is just a slit between a sandbar and a sand point but it is well marked and the controlling depth is around 10 feet. Once in, the anchorage lies to the southeast of Taylor’s Island.

Coecles Harbor Marina and Boatyard, builders of the Shelter Island 38, is a full-service yard on the western shore. Check the depth before you go. Full-keel boats must pay close attention to the tides. The Ram’s Head Inn to the north may have moorings (check with them first as the Inn has recently changed hands). Experience the sunset from here with cocktail in hand. It’s a local ritual.

West Neck Harbor is on the southern side of Shelter Island. A calm anchorage is against the sandspit. Dinghy ashore to hunt for shells or have a swim in warm waters. To the north is The Island Boatyard, where you can find a few slips, a marina with fuel, a restaurant and a popular bar.

The major anchorage is in Dering Harbor on the northern shore. This deep harbor (controlling depth is 20 feet) is a hubbub of activity. Members of a yacht club can check to see if they have reciprocity with the Shelter Island Yacht Club. If so, there are lots of transient moorings and a launch service. New owners have purchased Jack’s Marine; mooring availability is unclear at the time of this writing. Fuel can be obtained at Piccozzi’s dock. You can dinghy over to a small town landing if you want to visit the handful of businesses that comprise “downtown.” There are a few restaurants, hardware stores, a post office and several realtors. The renovated Chequit Inn has long been an island favorite. For a traditional breakfast with a Mexican accent try Stars Café. The espresso is pretty good.

To further explore the island, rent bikes at Piccozzi’s. Take one to the 2,000-acre Mashomack Preserve for an immersion in nature. Its well-marked trails vary in length from 45 minutes to 3 hours. Views from the bluffs on the blue trail are spectacular, with the whole of Gardiner’s Bay on display. If you are on a bike, the island’s beaches are open to you. I think the best swimming is on Menhaden Beach, but
family-friendly Wades Beach with a lifeguard and facilities is popular too.

GREENPORT Another advantage of staying in Dering Harbor is the ability to ferry access to Greenport. Once across, the entire North Fork of Long Island is accessible for exploration. With transportation, wine lovers can spend a few days visiting tasting rooms. Greenport itself boasts more than 20 restaurants and bars. The upgraded Claudio’s, which first opened in the 1870s, has dockside dining and cocktails. Greenport is a good place to provision as there are groceries and maritime supplies. Preston’s is a must for the latter.

With so much beauty and so much to see and experience, it’s no wonder the enchanting Gardiner’s Bay and the adjacent cruising grounds have been so popular with boaters for so long. 

This article was originally published in the April 2022 issue.

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