You are the owner of this article.

10 Northeast Island Getaways You'll Want to Get Stranded On

  • 5 min to read

You don’t have to fly to the tropics to enjoy the remote charm of an isolated island. These picturesque escapes are all within striking distance of Connecticut, so head to the closest ferry and get ready to kick back, crack open the rosé and disconnect from mainland stresses.

shutterstock_153697100.jpg

Nantucket, Massachusetts

Nantucket, Massachusetts

Travel back in time to Nantucket Island, just 30 miles off the coast of Cape Cod. Accessible by ferries from Harwich Port, Hyannis and New Bedford, Massachusetts, Nantucket’s sandy beaches, historic lighthouses and Main Street boutiques are straight out of a postcard. Traverse the island by bicycle, nosh on lobster rolls — critics say the best ones are served up at Cru and B-ACK Yard BBQ — and imbibe on local sips from Cisco Brewers, Nantucket Vineyard and Triple Eight Distillery, the island’s all-in-one distillery, brewery and winery. But most of all, don’t rush; life moves a little slower here. Suggested stay: Periwinkle Inn, 9 N. Water St., Nantucket, 508-332-4837, periwinklenantucket.com. Average peak season room price: $200-$375.

1661_Inn_Block_Island_3f2e892e-6757-4b6d-8768-19dffd2c9072.jpg

The 1661 Inn on Block Island, Rhode Island

Block Island, Rhode Island

Departing from New London, an 80-minute ride on the Block Island Express transports vacationers to a storybook world — where bicycles are the preferred method of transportation and chowder is the meal of choice. Visit the Southeast Lighthouse, first constructed in 1875, and the scenic Mohegan Bluffs, also a pre-Colonial battle site. Stay the night at one of the island’s many inns and B&Bs oozing with old-town charm, like Ballard’s Inn, tucked in the center of Old Harbor, steps from the ferry dock. Suggested stay: The 1661 Inn, 5 Spring St., New Shoreham, Block Island, 800-466-2141, blockislandresorts.com. Average peak season room price: $275-$599.

DSC_0445.jpg

A view from Fishers Island, New York.

Fishers Island, New York

Ferry service from New London and weekday commuter boats from Noank carry passengers to the resort-like Fishers Island, one of the Northeast’s best-kept secrets. The quiet, unspoiled respite serves as a summer destination for the nation’s elite — Keans and du Ponts, among them — and is home to private Hay Harbor Club and the golf destination Fishers Island Club. Even on holiday weekends, daytrippers can enjoy uncrowded beaches for sunbathing and fishing. Living up to its name, the island’s waters house bluefish, flounder, porgy, rock bass and butterfish. Suggested stay: The Big House bed and breakfast, New London, airbnb.com (there are no overnight accommodations on Fishers Island). Average peak room price: $50. 

Star Island dock w Laighton_ Bridgette Desmond.jpg

Star Island, New Hampshire

Star Island, New Hampshire

One of the nine Isles of Shoals off the coast of New Hampshire and Maine, Star Island has a storied history as a fishing port turned intellectual haven. Today, boaters can reach the island via a free tender service from Gosport Harbor. No yacht? Ferry services are located in Portsmouth and Rye, New Hampshire. Once here, visitors can explore Gosport Harbor by kayak, enjoy a meal in the historic Oceanic Dining Room or take an eye-opening environmental workshop. In the evening, don’t miss the stunning shorefront sunset. Suggested stay: Oceanic Hotel, Star Island, Isles of Shoals, 603-601-0382, starisland.org. Average peak season room price: $205 for meals and lodging.

shutterstock_1222182391.jpg

Shelter Island, New York

Shelter Island, New York

Shelter Island’s population of 2,400 multiplies to five times that each summer, attracting part-timers with its historic Victorian houses, osprey-inhabited wetlands, scenic beaches and sprawling golf courses. Tucked between the North and South forks of Long Island, Shelter Island is accessible by a short ferry ride from Greenport, which can be reached by ferry service out of New London. On the weekend, visit the Saturday farmers market at the Shelter Island Historical Society, then take a two-hour kayak tour from Coecles Harbor with Shelter Island Kayak. End the day with a glass of rosé at Sunset Beach, a hotel and restaurant on Shore Road. Suggested stay: The Chequit, 23 Grand Ave., Shelter Island Heights, Shelter Island, 631-749-0018, thechequit.com. Average peak season room price: $275-$475.

32-mile-long barrier island protects Long Island's populous southern shore from the open Atlantic.

Fire Island National Seashore, New York.

Fire Island, New York

Fire Island is at once a humming tourist destination and undiscovered treasure trove of natural wonders. Part of Long Island towns Babylon, Islip and Brookhaven, the thin, barrier island off the south shore is home to several state parks, the rare ecological community of Sunken Forest and 17 car-free communities at its center. Ferry service runs from Bay Shore, Sayville and Davis Park to reach the island’s various communities. Visit Ocean Beach for a bustling downtown and lifeguarded oceanfront or reach Cherry Grove and Fire Island Pines for stretching boardwalks and a rich LGBT culture. Suggested stay: A Victorian on the Bay B&B, 57 S. Bay Ave., Eastport, Fire Island, 631-325-1000, victorianonthebay.com. Average peak season room price: $275-$400.

Chebeague_Island_September_2016.jpg

Chebeague Island in Maine's Casco Bay.

Chebeague Island, Maine

The Casco Bay island of Chebeague is just 2 miles by ferry from Yarmouth, Maine. “The isle of many springs,” Chebeague is dotted with Greek Revival homes reflective of its sailing history. Today, the neighborly community is home to a boatyard, museum and a waterfront nine-hole golf course. After coffee at the Slow Bell Cafe, visit Deer Point for classic Maine views of rocky ledges and dark pines. Then, sunbathe on the sandy Hamilton Beach before taking in the sunset over a porchfront cocktail at the historic Chebeague Island InnSuggested stay: Chebeague Island Inn, 61 South Road, Chebeague Island, 207-846-5155, chebeagueislandinn.com. Average peak season room price: $200-$350.

Thimble Islands.01.jpg

The Thimble Islands off the Branford coast.

Thimble Islands, Connecticut

The Thimbles are a group of small islands off the southeast corner of Branford in the picturesque Stony Creek Harbor. In the summer, they can be accessed by the Thimble Island Ferry Service or via sightseeing cruises and private charters from Thimble Islands Cruise. On a 45-minute narrated tour, visitors learn about the islands’ natural history and the booming shellfish industry of the Victorian Era. For the adventurer, rent a kayak or paddleboard from Branford River Paddlesports and thread your way around the islands. Finish the day with a craft beer from one of Branford’s popular breweries, Stony Creek and Thimble Island. And if you want to lengthen your stay, check out one of the homes to rent on Airbnb and other rental sites, or stay in one of the B&Bs along the shore. Suggested stay: Thimble Islands Bed & Breakfast, 28 West Point Road, Stony Creek, Branford, 203-488-3693, thimbleislandsbb.com. Average peak season room price: $300-$400.

6963585130_e81e999ec3_o.jpg

Martha's Vineyard, Massachusetts

Martha’s Vineyard, Massachusetts

Colloquially called “The Vineyard,” this island just a 45-minute ferry ride from Cape Cod is one of the largest on the East Coast. It charms with picture-perfect sandy beaches, bright gingerbread cottages, farmers markets and lighthouses. Visit the Flying Horses, the nation’s oldest performing carousel, and keep your eyes peeled for celebs like Bill Gates and Oprah Winfrey. Or, let your stomach lead you and take Farm.Field.Sea’s culinary day trip connecting sea and soil farmers with food educators and, of course, local eats. Suggested stay: Vineyard Square Hotel & Suites, 38 N. Water St., Edgartown, Martha’s Vineyard, 508-627-4711, vineyardsquarehotel.com. Average peak season room price: $275-$500.

shutterstock_313128515.jpg

The Bass Harbor Head Lighthouse in Acadia National Park on Mount Desert Island, Maine.

Mount Desert Island, Maine

A recent Vogue article declared that Mount Desert Island “might be the most beautiful spot in New England.” Locally referred to as MDI, the island is largely covered by Acadia National Park. Wild blueberry bushes line the many walking paths leading to breathtaking oceanfront cliffs. Along with the natural sites, visitors here can enjoy shopping at charming boutiques in Bar Harbor and dining on every kind of seafood. Head to Thurston’s Lobster Pound to enjoy fresh-off-the-boat lobster overlooking the harbor from which they were harvested. Suggested stay: Asticou Inn, 15 Peabody Drive, Northeast Harbor, Mount Desert Island, 207-276-3344, asticou.com. Average peak season room price: $175-$350.


More Summer Travel Ideas:

This article appeared in the July 2019 issue of Connecticut Magazine. You can subscribe here, or find the current issue on sale hereSign up for our newsletter to get the latest and greatest content from Connecticut Magazine delivered right to your inbox. Got a question or comment? Email editor@connecticutmag.com, or contact us on Facebook @connecticutmagazine or Twitter @connecticutmag.