The Fairest Isles of Them All

From quaint to rugged, urban to completely off the beaten path, New England’s archipelago is all over the map. These are the places worth leaving the mainland for.


Block Island, Rhode Island

HOW TO GET THERE | Ferry service runs from Narragansett, Newport, and Fall River.

THE VIBE | Blissfully chilled out (it’s nicknamed the “Bermuda of the North”) and bikeable.

WHERE TO EAT | Housed in a charming gray-shingled building, Eli’s eschews summer staples like fried clams and chowder in favor of niçoise-style seared tuna and steaks with foie butter.

WHERE TO STAY | One of the island’s most iconic properties (it’s hosted the likes of Mark Twain and Ulysses S. Grant), the Spring House Hotel debuted a shiny new boutique inn on the property in 2015.

WHERE TO PLAY | Soak up the scenery (and get your daily steps in) with a visit to Mohegan Bluffs, 185-foot-tall clay cliffs that descend via steep stairs to a sparkling beach.

Photograph by Ashley Caroline

Peaks Island, Maine

HOW TO GET THERE | A 20-minute ferry departs from Portland’s waterfront 14 times a day.

THE VIBE | Decidedly no-frills and home to a rugged, close-knit community that balloons in the summertime.

WHERE TO EAT | One of a handful of restaurants on the island, the Cockeyed Gull is the only one open year round.

WHERE TO STAY | The Inn on Peaks Island is rich with elegant curb appeal among the island’s modest cottages. Six suites boast cathedral ceilings and fireplaces, not to mention private decks framing views of the Portland skyline.

WHERE TO PLAY | Trace Peaks’ rocky coastline on a bike rented from Brad’s Bike Rental & Repair (pro tip: opt for a tandem if you’re exploring with a pal). A trip around the 720-acre island takes about an hour, leaving plenty of time for a quick visit to the world’s only Umbrella Cover Museum.


Vinalhaven, Maine

HOW TO GET THERE | Ferry service runs from Rockland, Maine, daily—or hop on Penobscot Island Air’s 10-minute flight from Owls Head.

THE VIBE | A quaint, quiet lobstering enclave with ultra-friendly neighbors.

WHERE TO EAT | Seafood’s the star of the plate at Salt restaurant, which offers surprisingly sophisticated takes on Maine classics—think poached Vinalhaven lobster with Thai-coconut beurre monté and black rice.

WHERE TO STAY | Built on a bridge above Carver’s Harbor, the aptly named Tidewater feeds off the ebb and flow of the water beneath it. Accommodations are simple—all the better to focus on the views.

WHERE TO PLAY | Take a dip in the former granite quarries. Enjoy a long, contemplative walk in the nature preserves. Or do absolutely nothing at all—that’s the beauty of island life.


The Boston Harbor Islands

HOW TO GET THERE | Boston Harbor Cruises boats depart from Long Wharf daily.

THE VIBE | Otherworldly, considering the city is visible from the island chain’s shores; brimming with history, flora, and fauna.

WHERE TO EAT | The snack stands on Spectacle and Georges islands joined forces with chef Barbara Lynch last year, resulting in some seriously elevated noshing options. Don’t miss the signature lobster roll.

WHERE TO STAY | If you manage to book early enough, the yurts on Peddocks Island offer a novel rustic retreat. Equipped with a screen door, bunk beds, a dining set, and the relative luxury of electricity, the tented cabins are the closest you’ll get to glamping in the city.

WHERE TO PLAY | Roam the cavernous corridors of Fort Warren on Georges Island, then catch a vintage baseball game (players don Civil War–era uniforms) on its parade ground.

More from our Escape to the Islands feature.