Choosing the best islands in New England is like picking your favorite ice cream—each one is unique and delightful in its own way. Every island boasts beautiful landscapes, distinct attractions, and a personality shaped over centuries. Instead of debating which is superior—Nantucket or Martha’s Vineyard—plan a visit to them all so you can decide which one truly steals your heart.
Aquidneck Island, the largest in Narragansett Bay, is conveniently connected to the mainland by bridges, making it easy to overlook that it’s an island at all. With the city of Newport and the towns of Portsmouth and Middletown, known for their charming waterfronts, Aquidneck is more like a stopover than an out-of-the-way retreat. This accessibility means no excuses for missing its must-see sights.
In Newport, explore grand Gilded Age mansions, wander the scenic Cliff Walk, shop and dine by the harbor, and perhaps embark on a sailing adventure in the “Sailing Capital of the World.” Middletown offers the island’s best beaches and Flo’s Clam Shack’s famed fried clams. Don’t forget Portsmouth, where the Green Animals topiary garden and Rail Explorers provide unique family adventures along historic tracks by the bay.
Maine’s Mount Desert Island, larger than the rest on the East Coast except for New York’s Long Island, is home to much of Acadia National Park’s 47,000 acres. Known for its sandy beaches, ocean-carved cliffs, and granite peaks like Cadillac Mountain—the highest point in the East Coast—this island is connected to the mainland for easy access. It’s a hotspot for cruise ships and worth visiting for Acadia alone.
Acadia offers endless recreational opportunities year-round, but Mount Desert Island has more to discover in the bustling town of Bar Harbor. Here, you’ll find top-notch hotels, delightful eateries, and the opportunity to embark on whale-watching tours or savor lobster ice cream—all amidst learning about the native culture of the region.
Martha’s Vineyard, Massachusetts’ largest offshore island, accessible only by plane, ferry, or your own yacht, carries an air of mystique. Celebrities like the Obamas, Clintons, and Kennedys have all escaped to this island’s blend of exclusivity and diversity over its 96 square miles.
Even a short visit lets you enjoy classic Vineyard experiences like cycling past Oak Bluffs’ whimsical gingerbread cottages, riding the Flying Horses Carousel, and sipping Bad Martha beer while admiring Edgartown’s iconic lighthouse. If you can linger longer, venture to Menemsha for affordable seafood or soak in Aquinnah’s famous Gay Head Cliffs’ stunning views.
A 30-mile journey offshore brings you to Nantucket, New England’s most isolated island. It’s chic and sophisticated, yet leisurely, with a year-round community that cherishes traditions from the spring Daffodil Festival to the Christmas Stroll. With the whole island designated as a National Historic District, Nantucket boasts one of the largest collections of pre-Civil War homes in the nation.
The Whaling Museum and Maria Mitchell Association are must-visits, offering stargazing nights with experts. No Nantucket trip is complete without basking on its beautiful beaches, biking to ‘Sconset, tasting drinks at Cisco Brewers, and grabbing a seat at Black-eyed Susan’s.
Block Island, or New Shoreham, sits about 9 miles from Rhode Island’s coast and it’s an ecological wonder, with nearly half its area preserved. Its Caribbean-blue waters and distinct geography make it a gem, though bringing a car can be tricky. Local taxis accommodate arrivals, and the island’s Victorian inns, shops, and eateries are just a stroll away from the ferry dock.
Don’t miss the Southeast Light atop the storied Mohegan Bluffs, with wooden steps leading to a secluded beach that’s the opposite of lively Ballard’s Beach, where live music and drinks service create a different vibe.
Monhegan Island in Maine, a mere square mile in size, captivates artists with its reflective light and quintessential New England charm. Reachable by ferry, it’s rich in artistic heritage, with studios, an art museum, and opportunities for plein air painting. Monhegan also offers 12 miles of hiking paths, quaint inns, shops, and restaurants. Although swimming waters may be chilly, hunting for sea glass is a rewarding pastime.
Vermont, despite lacking an ocean coastline, boasts islands in Lake Champlain. North of Burlington, Route 2 leads to the connected communities of South Hero, Grand Isle, North Hero, and Isle La Motte. This underrated Vermont retreat features beaches, bike paths, state parks, and landmarks like Hero’s Welcome and the Chazy Fossil Reef at Fisk Quarry Preserve.
In Boston, escape without ever leaving the city. Sign up for a Boston Harbor Cruises ferry tour to several islands in the Boston Harbor Islands National Park. Spectacle Island, reached in 20 minutes, offers clean beaches, perfect for swimming, picnicking, and hiking.
More adventurous travelers can visit Georges Island—a 45-minute ferry ride away—to explore Fort Warren’s Civil War ruins or join ranger-led programs while enjoying historic and active Boston Harbor views. The Harbor Islands also offer camping on islands like Bumpkin, Grape, Lovells, or Peddocks.
The charm of an island seems to multiply with the challenge of reaching it, and Chebeague Island in Maine is a good example. Choose between a leisurely Portland ferry trip taking 60-90 minutes or a speedier option from Yarmouth that cuts the trip to 15 minutes but requires shuttle bus logistics. Chebeague’s 24-square-mile landscape, with just 350 year-round residents, is a rewarding destination with the century-old Chebeague Island Inn to welcome you.
Don’t miss the Chebeague History Museum, the nine-hole waterview golf course at Great Chebeague Golf Club, and scenic beaches for carefree hours on this bike-friendly island.
The Isles of Shoals off New Hampshire and Maine’s coasts intrigue visitors with their whimsical names: Appledore, Cedar, Duck, and more. Roughly 10 miles offshore, these sparsely populated islands brim with stories and legends.
Portsmouth-based Isles of Shoals Steamship Company offers narrated cruises filled with tales of pirates and ghosts. For a day trip, cruise to Star Island for its Victorian-era Oceanic hotel or relax with a lobster roll against the historic backdrop.
