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Seclusion and the Sea
LESLIE LONG trolls up and down the coastal Northeast, in search of island life as it used to be.

Some say that Nantucket is sinking under the weight of new construction, that Block Island often sounds like a motorbike derby and that Shelter Island, thanks to the arrival of an Andre Balazs hotel, is shedding its common touch.

What’s an island lover to do? Read on, for one thing. If you dream of old clapboard hotels with wraparound porches, lazy days at uncrowded beaches and seafood dinners where you need an appetite, not a reservation, here are three amazing islands just for you.


Fifteen minutes by ferry from Portland, Maine, is an island so untouristy, you can’t even rent a bike. Instead, you can get one gratis by stopping at the house of a man known by everyone on Chebeague. Just ask for the bike guy.

About 3 miles long and 11 miles wide, this friendly island of birches and pines has just one town. Stop by the Artisan’s Ice House for trinkets, fish off the ferry dock, jump in the water for an icy dip and golf at the nine-hole Great Chebeague Golf Club (open to the public weekdays, and Sundays after 2p.m.; golfable.com).

STAY: There are several lodging options, including the amazing Chebeague Island Inn. This old, clapboard treasure has just been renovated into a stylish boutique-like hotel — minus the pretentiousness. It’s the only place on the island that serves dinner, so luckily the food is fab. Get there early for cocktails in the bar (rooms from $185/night: chebeagueislandinn.com).

INFO: For ferry schedules from Portland, visit cascobaylines.com; for ferries from Yarmouth, use chebeaguetrans.com; for general info, check out visitmaine.com.


For unbelievably wide open spaces, and place where a traffic jam consists of a golf cart and a tractor, go straight to Cuttyhunk.

Board the ferry “Alert” in New Bedford, Mass. (southeast of Providence, R.I.), and in under an hour you’ll find yourself amid this island’s gray-shingled summer houses, looking out at sweeping water vistas and endless sky.

Only one-third of the two-mile long, one-mile wide island is settled. Lots of boaters dock here on their way up and down the coast to bird watch, walk the beaches and island trails, and hang out around the Fish Dock (the town marina). Stop in at the Sea Girl for souvenirs, and the Pea In Your Pants gallery for art.

Also, make sure to walk gorgeous Rocky Beach. To sunbathe, Church’s Beach is your spot. For lunch only, the Fish Dock offers Cuttyhunk Raw Bar for chowder and clams, and Nashaweiner for burgers and dogs. Only the pizza parlor serves dinner, but at least you’ll dine at a picnic table next to croaking bullfrogs.

STAY: The island’s only hotel is the historic, wonderfully plain Cuttyhunk Fishing Club (from $135/night; cuttyhunkfishingclub.com).

INFO: For island and ferry info, visit cuttyhunk.com


If you’ve eaten a soft shell crab in New York, it was probably snagged near Smith Island.

Maryland’s only inhabitable offshore island in the Chesapeake Bay is mostly home to several hundred watermen (the local name for crabbers) and their families — and has been for centuries.

There are two main towns here, Ewell and Tylerton. Ewell, the busier of the two, is where the mainland ferry stops. It’s got a ton of worn charm, and the new Museum and Cultural Center for island lore.

Tylerton has a simple, old-fashioned appeal. Rent bikes and kayaks at the Inn of Silent Music (info below). And while there are no beaches, there are plenty of places to hang out by the water.

For lunch, try Drum Point Market for its famous crab cake.

STAY: The Inn of Silent Music , which serves extraordinary breakfasts and dinners on its screened-in porch (from $105/night, Tylerton: innofsilentmusic.com), or the friendly Ewell Tide Inn (from $50/night; smithisland.net).

INFO: smithisland.org