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TravelLong Island Getaways

Fishers Island, Shelter Island and other offshore destinations

You know Jones Beach Island, Long Beach and Fire Island, but there are quite a few other islands to explore on Long Island’s 120-mile coastline. From Meadow Island on the South Shore to Fishers Island at the eastern entrance of Long Island Sound, a treasure trove of smaller islands range in size from townships to islets with only enough acreage for a lighthouse.

Execution Rocks Light Station

Visitors look off the side of the water
Credit: Steve Pfost

HISTORY This rock pile in Long Island Sound was constructed in 1840, on top of an earlier rock pile that gave the island its morbid moniker. According to local legend, British occupiers executed American patriots during the Revolution by shackling them on the rocks to drown in the rising tide. The lighthouse tower was erected in 1849. Craig W. Morrison, president of Historically Significant Structures, bought the island in 2009 from the federal government and is raising funds to restore and preserve its historic lighthouse.

GET THERE The island is not open for group tours. But Morrison’s organization offers overnight stays in the keepers quarters, or, with special permission, in the lighthouse tower ($250-$350 a night). Guests are provided air mattresses and potable water, but need to carry in most everything else. Transportation to the island is arranged by Morrison with Long Island Boat Rentals, at $100 per person round-trip.

THINGS TO DO Make the most of having no Wi-Fi, electricity or running water. Fish (bring your own bait and tackle), read, sunbathe, go kayaking or hang out with Morrison to learn more about local maritime history. For a Gatsbyesque thrill, gaze across the water at the island’s neighbors, whom Morrison calls the “billionaires of Sands Point.”

INFO 215-906-5103,

Meadow Island

Boaters head towards the docts to visit homes
Credit: Johnny Milano

HISTORY Located in the western bays of Nassau County’s South Shore, near Jones Beach Inlet, the cast of characters on Meadow Island since the 1800s has included commercial fisherman, Prohibition rumrunners, professional musicians, theater actors and guests in a now long-gone hotel. Five bay houses survived devastation from superstorm Sandy.

GET THERE Long Island Traditions, a Port Washington-based nonprofit preservation organization, hosts three-hour “Boating with the Baymen” tours around the island from Freeport (details at 516-767-8803,

THINGS TO DO Meadow Island’s lush tidal wetlands are crowned by spectacular sunsets. But it’s privately owned, so you can’t just drop in. But residents of its cottages facing the bay won’t mind if you wave while cruising by on your pleasure boat. You can meet a number of them in person on a Long Island Traditions tour. By the bye, you may have already visited Meadow Island without knowing it: The Loop Parkway to Point Lookout runs through it.


Taylor’s Island

Taylor's Island, an island, owned by Shelter Island.
Credit: randee daddona

HISTORY Originally called Cedar Island because cedar trees thrived on its sandy ground, this 1-acre oasis in Shelter Island’s Coecles Harbor was purchased around the turn of the 19th century by borax miner Francis Marion Smith. Smith built a one-room cabin on it as a family retreat. Hotel magnate S. Gregory Taylor bought the island in 1937, added amenities to the cabin and renamed it Taylor’s Island. The Town of Shelter Island took possession of the island 20 years ago through a stipulation in Taylor’s will. Listed on the National Register of Historic Places, it’s maintained by the Taylor’s Island Preservation and Management Committee.

GET THERE First you need to get to Shelter Island. Then you can launch a boat from the town dock at the end of Congdon Road or a kayak from Coecles Harbor. Shelter Island Kayak Tours offers rentals — ask for a map of the five-mile Coecles Harbor Marine Water Trail, which takes about three to four hours to paddle. Another option: Call ahead (631-749-1603) for a ride to the island on the Taylor’s Island Preservation and Management Committee Boston Whaler — aka Taylor’s Whaler — says P.A.T. Hunt, co-chair of the committee and president of the Taylor’s Island Foundation.

THINGS TO DO The committee offers a free docent-led tour — also by telephone reservation — of Taylor’s Island’s only structure, the Smith-Taylor log cabin, which is under restoration.

INFO 631-749-1603,

Shelter Island

The main house at the Sylvester Manor on
Credit: Gordon M. Grant

HISTORY The 12-square-mile island between the North and South Forks was originally the ancestral home of the Manhanset Indians. For most of its early history the island was owned by prominent families including the Sylvesters, Havenses and Nicolls. During the American Revolution and again in the War of 1812, the island was ransacked from British warships that anchored in the bays.

GET THERE Take the ferry from Greenport ($3-$16, 631-749-0139, or from North Haven ($1-$17, 631-749-1200,

THINGS TO DO Shelter Island offers all the fun and amenities of an upscale resort community, including luxury hotels, restaurants and boutiques. Take a bike tour along Shelter Island’s Victorian-home-lined shady country lanes with your own two-wheeler or a rental from Piccozzi’s Bike Shop (631-749-0045, Explore local history at The Sylvester Manor Educational Farm, a onetime slave plantation reborn as a nonprofit organic farm and arts and education center (631-749-0626, Or commune with nature on a hike through the Nature Conservancy’s breathtakingly beautiful 2,039-acre Mashomack Preserve (631-749-1001, Bring a bathing suit and a beach read to Crescent Beach or Wades Beach, exclusive spots for sunbathing and lifeguard-protected swimming.

INFO 877-893-2290,

Fishers Island

A handful of shops in the business district
Credit: Randee Daddona

HISTORY For most of its history the island was used for dairy farming and raising livestock. Its colorful past also includes plundering by pirates and — because of its strategic location — raids by British troops, who torched all the houses and crops during the American Revolution. Development began in the 1870s but was curtailed by the Great Depression, which “kept the island from being overdeveloped,” says Pierce Rafferty, director of the island’s Henry L. Ferguson Museum. 

GET THERE Fishers Island is a Town of Southold hamlet, but it’s closer to southeastern Connecticut. There’s a 45-minute ferry there from New London, Connecticut (860-442-0165, 

THINGS TO DO With no public lodgings, Fishers Island is only a day trip. Two-thirds of the island’s approximately 3,000 acres are privately owned, by about 230 year-round residents who guard their privacy on the other side of a gatehouse. The island “does nothing to encourage people to come from the outside world,” Rafferty says. The west end is where you’ll find a New England-style town green and public accommodations such as a grocery store, cafe and The Pequot Inn bar and restaurant, the latter open only during the late spring and summer months. The Henry L. Ferguson Museum is also open to the public, with collections focusing on natural history and archaeology (631-788-7239, 


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