When many travelers think of exploring U.S. island destinations, it’s often the tropical variety that comes to mind. But as stunning as the Virgin Islands or Hawaii are, islands off the coast of New England are equally exquisite, offering captivating views, outdoor adventure, windswept beaches, and centuries-old architecture. In a region known for quaint towns, authentic charm, and rich history, New England’s unspoiled beauty is nowhere better embodied than on these interesting and alluring islands out to sea.
To help plan the ultimate coastal travel itinerary in this part of the country, here are the best islands in New England that should be on your radar for a trip to remember.
1. Nantucket, Massachusetts
It’s hard to imagine a New England island vacation without Nantucket topping the list. This charming island in Massachusetts, known as the Gray Lady for its thick, rolling fog and gray saltbox houses, is 30 miles out to sea and a world away.
Making its name in the mid-18th century as the whaling capital of the world, Nantucket’s history is evident today around every cobblestone street corner, starting with the Nantucket Whaling Museum. This cultural gem tells the story of the island’s past, its rise to economic prosperity, and its reckoning with the controversial practice of whaling that came to an end in the mid-1800s.
You won’t find a single big-box store on the island, nor is there any need to travel here with a car. You’ll save time and money by leaving your vehicle behind! (You can park at ferry departure points including Cape Cod, New Bedford, Mass., and New York City, depending on the time of year.)
Nantucket’s downtown, chock-full of quaint shops and locally owned eateries, is easy to explore on foot. Rent a bike to discover the treasures of mid-island, including Bartlett’s Farm, which is perfect for grabbing lunch or packing provisions for a picnic. The farm is nearby Nantucket Vineyard and the iconic Cisco Brewers, a compound where kids, dogs, and visitors from all walks of life are welcome.
A day trip will suit travelers on the go, but for overnight or weekend getaways, renting a jeep will allow you to explore more of this beautiful island’s 48 square miles.
2. Chebeague Island, Maine
There are more than 3,000 islands in Maine, each boasting its own beauty, but Chebeague is one of the most stunning and most easily accessible. Located just 10 miles off the seaport city of Portland, the most populous city in Maine, Chebeague (pronounced “shuh big”) is one of the famed Casco Bay Islands.
Getting there is half the fun – the ferry ride from Portland is a little over an hour, and the natural beauty of the cobalt blue bay combined with the views of the island will capture your heart as you approach State Ferry landing at Chandler’s Cove.
Early Native Americans settled this island, where fishing is plentiful and lobsters abound. In the 1800s, the island carved out a name for itself as colonial-era “stone sloopers,” men who carried ballast for the sailing ships and granite that would form many of America’s famous landmarks, became the cornerstone of the island’s economy.
Today, visitors can take in the impressive Greek Revival homes that remain intact from the era. The Chebeague Island Inn seems to be a step back in time, with its sprawling wrap-around porch positioned to admire the view of the bay.
Borrow a free bike from the Bikeman to explore the island, but not before enjoying a lobster roll under a canopy of trees at Calder’s Clam Shack.
3. Aquidneck Island, Rhode Island
The largest island in world-renowned Narragansett Bay, Aquidneck Island is home to the town of Portsmouth, Middletown, and the well-known City of Newport. Known for its legendary maritime history, Gilded Age mansions, and the most intact and well-preserved collection of colonial homes and buildings in the U.S., Newport lures visitors to the smallest state in the country the whole year through.
From 1930 to 1983, Newport hosted the famed America’s Cup sailing races, and today you can enjoy a sail aboard one of the Cup’s 12-meter competitors. A cruise through Newport Harbor on one of these yachts or one of the many other vessels available for tours will showcase some of the best views the coastal enclave has to offer, including Hammersmith Farm, the summertime familial home of Jacqueline Bouvier, wife of John F. Kennedy.
Newport’s neighbor to the north, Middletown, is home to a trio of popular beaches, including Sachuest Beach (locals call it “Second Beach”). The northern end of the beach, known as “Surfer’s End,” draws wave-riders during every season. Middletown is also home to Newport Vineyards, a Napa-esque winery featuring live music, fire pits, and culinary events celebrating local flavor.
Portsmouth boasts Aquidneck Island’s coastal pastures and farmland, including Glen Farm, home to the Newport International Polo Series during the summer through early fall. Competitors from around the world entertain tailgaters and enthusiasts as they take part in “the sport of kings,” which has been played here since 1886.
4. Martha’s Vineyard, Massachusetts
The Obamas and the Clintons might have been the presidents that put this summertime playground on the map, but they weren’t the first American chief executives to visit Martha’s Vineyard. Presidents Grant, Coolidge, Roosevelt, Cleveland, and Nixon – and even John Adams – visited this captivating island gem.
There’s a reason “the Vineyard” has been dubbed “Hollywood East” – politicos and celebrities have fallen for the island’s dramatic cliffs overlooking the sea, its preserved 19th-century homes and buildings, its ample culinary treasures, and its simple joys.
Unspoiled beaches can be found across the island, including Katama Beach (also called South Beach), a free beach open to the public that extends for three miles and allows vehicles with permits on marked trails. (It is one of two “drive-on” beaches on the island.) Biking is also a great way to get to the beach or around the island, as there’s a serene bike path along Katama Road.
The Aquinnah Cliffs located on the western edge of the island are a must-see, with captivating views and the stoic Gay Head Light, which reaches 170 feet into the sky.
Nearby, the tiny village of Menemsha is as lovely as it is laid back, and should look familiar to any fan of the movie JAWS. You’d be remiss if you left without a take-out container of creamy clam chowder from Larsen’s Seafood Market on Menemsha’s docks.
In Oak Bluffs, the commercial center of the island, you’ll find the famous colorful gingerbread cottages with elaborate century-old architectural detail. Martha’s Vineyard is hands-down one of the best islands to visit in New England.
5. Grand Isle, Vermont
Vermont’s idyllic Champlain Islands are made up of five lakeside communities within Lake Champlain, resting between Vermont and New York. Nestled into the northwest corner of Vermont, just 90 minutes south of Montréal, Canada, and a half-hour drive from Burlington, the shining star of the Champlain Islands is Grand Isle, also known as South Hero Island.
The largest and most populous island of the archipelago, Grand Isle is an outdoor-lover’s paradise, ideal for kayaking, camping, boating, fishing, and more alfresco exploits. Grand Isle State Park is a 226-acre expanse (and the most popular campground in the state) that affords miles of inspiring hiking and biking trails, lush greenery, and beautiful wildflowers.
The island is also home to Hyde Log Cabin, a historic house museum that is said to be one of the oldest log cabins in the country.
Snow Farm Vineyard, boasting a spectrum of award-winning craft wines, is a hub of activity in the summer with a popular evening concert series. By early fall, Hackett Orchard comes alive, welcoming guests to pick apples of 47 different varieties or simply to enjoy the family-run farm on an orchard tour or wagon ride.
Most visitors to the farm can’t resist the temptation of tasting some warm cider donuts and hot apple cider made on site, or to take home a bottle of the farm’s pure maple syrup.
6. Vinalhaven Island, Maine
Maine is known for so many things, most notably lighthouses, lobster, and untouched natural beauty beyond compare. Of the more than 4,600 islands in New England’s northernmost state, Vinalhaven is the largest and one of the most beautiful islands in Maine.
With a small but mighty year-round population of just over a thousand, the island does have more conveniences than some other Maine islands, including a few restaurants and shops in addition to an inn (and plenty of Airbnbs).
Perched in the middle of beautiful Penobscot Bay, the mainland terminus for the Vinalhaven ferry is in Rockland, and the 15-mile scenic trip takes a little under 90 minutes. The ferry runs year-round, with more options during peak season. As you cruise into port, you see no shortage of lobster boats bobbing in the harbor, as the fleet here hauls in tons of the savory crustaceans.
Granite was quarried here around the turn of the century, leaving behind two popular quarry ponds: Lawson’s and Booth’s. Both are ideal for kayaking, canoeing, paddleboarding, or taking a refreshing swim.
Back on land, nearly two dozen parks offer miles of hiking and walking trails and plenty of space to roam.
7. Block Island, Rhode Island
Just nine miles off mainland Rhode Island, Block Island rises from the sea, its magnificent clay bluffs making for a stunning greeting upon arrival. Leave the car behind – getting around is easy on foot, by bike or moped, or via plenty of rideshares. May through October is peak season for the island community, but it’s beautiful and accessible year-round.
An impressive 200 feet above sea level, Mohegan Bluffs are a sight to behold. And if you’re willing to climb down the steep but picturesque stairwell, your sweet reward will be the beach at the bluffs’ sandy base.
Other beaches include the secluded Mansion Beach, Crescent Beach on the eastern shore of the island, Scotch Beach (decidedly less crowded than the Town Beach), and the rocky shores of Gracie’s and Dorie’s Coves, which vie for the best sunsets on the island.
One of New England’s premier boating destinations, the Great Salt Pond on the west side of the island offers amazing views and ample opportunities for outdoor exploits. The striking 52-foot Southeast Lighthouse is a spectacular granite tower and an oft-photographed National Historic Landmark, so bring the camera.
8. Cuttyhunk Island, Massachusetts
The outermost of the Elizabeth Islands, Cuttyhunk is uniquely positioned between Buzzards Bay to the north and Vineyard Sound to the south. Though the island’s land area is less than one square mile, jaw-dropping natural beauty abounds here. Half of the main part of the island is a dedicated nature preserve and a bird watcher’s paradise, with lesser-seen birds migrating here like the rare Painted Redstart, usually found in Mexico.
The island’s small size makes it easily walkable, and rather than cars, you are far more likely to see the occasional golf cart, driven by one of the less than 50 island residents.
In the summertime, wildflowers usher in a cacophony of color, with ample bayberry, sweet peas, and other plant life offering vibrant hues amid the island’s grassy rolling valleys. Much of Cuttyhunk’s shoreline is rocky, but the beaches here offer soft sand and azure seas.
The best views are afforded at Lookout Hill, a naval lookout during World War II, rising more than 150 feet above sea level and offering lovely water views as far as the eye can see. From here you’ll also spot Martha’s Vineyard, just six miles away, and plenty of boats fishing the bounty of striped bass that populate these waters.
9. Thimble Islands, Connecticut
It’s hard to pinpoint just one of the Thimble Islands, as this picturesque island chain comprises 25 small islands that all share similar traits: rocky shorelines, wooded areas, and inspiring vistas.
Located in Long Island Sound just a few miles off Connecticut’s mainland coast, “the Thimbles” are mostly all private, save for Outer Island – a five-acre island that serves as an ecological preserve and refuge for migratory birds.
The best way to see and experience this outcropping of rugged islands is by boat, with a number of cruises that depart from the charming seaside village of Stoney Creek on the mainland, not too far from better-known New Haven.
The tall, captivating pines that rise along the islands are reminiscent of the Pacific Northwest, while the surrounding waters are ideal for sailing, kayaking, stand-up paddleboarding, and other fun activities like water skiing. On some of the islands, you’ll spy impressive and intricate summer cottages built during the Victorian Era.
10. Rose Island, Rhode Island
Perched in the middle of the East Passage of Narragansett Bay between Newport Harbor and the shoreline of Jamestown, Rose Island is best known for the lighthouse there that is the island’s namesake.
Maintained by a foundation dedicated to preserving and maintaining the historic and environmental integrity of the island and lighthouse, Rose Island’s 18.5 acres include a wildlife refuge, home to colorful migratory birds. In the winter months, you can see harbor seals sunning themselves on Citing Rock.
During low tide, you can walk out rather far into the bay, and the view from there is simply unparalleled. The island encompasses many walking trails, and you can explore the remnants of stone barracks built there during the American Revolution, as well as the areas that once stored explosives, warheads, and torpedoes manufactured at the former Naval Torpedo Station.
The best part is that you can stay in the Rose Island Lighthouse or the nearby Fort Hamilton Barracks building for up to a week, and at nighttime you can bask in the glow of the “pearl necklace” lights of the Newport Pell Bridge.
11. Star Island, New Hampshire
The largest of the famed Isles of Shoals that bestride the New Hampshire-Maine border, Star Island is a majestic gem gilded with rugged natural scenery all around. It is the only one of the nine Isles of Shoals that is accessible to the public, and only during the summer months.
The artists’ colony here has no shortage of inspiring vistas, surrounded by the island’s natural, unspoiled landscape. With a rugged shoreline, rolling green hills, and simple stone cottages, you could easily imagine you’re on the coast of Ireland, if only for a moment.
The Oceanic Hotel, a throwback to days gone by, is the most dominating building along the island’s skyline, encircled by a wraparound porch dotted with rocking chairs for visitors to take in the view. The old Gosport Chapel, built in 1800, looks frozen in time and stands majestically on the island’s highest point.
Flower-lined footpaths will guide you around the island, while interesting structures, including what looks like a mini-Washington Monument, will undoubtedly pique your curiosity.
12. Mt. Desert Island, Maine
It seems impossible to have a round-up of the most beautiful islands in New England without including Mt. Desert Island, most notably because it is home to lauded Acadia National Park. One of the top 10 most-visited national parks in the U.S., the park itself comprises 47,000 lush acres, a diverse topography, and an abundance of wildlife including moose, bear, and countless white-tailed deer.
Called the “crown jewel” of the North Atlantic coast, Acadia boasts the highest rocky headlands on this side of the country and more than 150 miles of trails to explore.
You can actually drive to Mt. Desert Island, and Acadia’s 27-mile Park Loop should be your first stop, allowing you to take in the rugged beauty of massive Cadillac Mountain (one of 18 mountains here) and the crystal blue waters of Jordan’s Pond and Thunder Hole. Keep an eye out for wild blueberry bushes to taste the local spoils of the land.
Maine’s largest island is also home to Bar Harbor, one of the most-visited destinations in the region, known for its quintessential and unforgettable New England coastal charm.
Rife with natural beauty, diverse landscapes, and classic American charm, the islands throughout New England are some of the most beautiful in the world. Whether for a day trip, a weekend getaway, or an extended stay, New England’s island destinations await your next adventure.
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