5 Maine Islands to Visit This Summer

By Yankee Magazine

Apr 23 2018


Squirrel Island

Photo Credit : Aimee Tucker
For “Hidden Gems” (season 2, episode 5), Weekends with Yankee traveled to Chebeague Island off the coast of Southern Maine to explore the island, visit its sole inn, and harvest local oysters. Here, Yankee digital editor Aimee Tucker highlights five favorite Maine islands, including Chebeague, that are well worth a visit. Island day-trips and getaways can be ideal escapes because they often require an extra boost of effort. It’s not simply a matter of putting in a few hours on the interstate. It’s an investment of time and, in many cases, a willingness to forgo more modern amenities — like access to a car, fine dining options for dinner, and air conditioning. But that investment yields some real rewards. A slower pace. A return to nature. An experience you’ll remember for years to come. Here are five noteworthy Maine islands to visit this summer. 


Chebeague Island Inn’s famously long porch, home to some of the finest sunset views in New England.
Photo Credit : Courtesy of Chebeague Island Inn

Chebeague Island | Casco Bay

Chebeague (pronounced sha-BEEG) is the largest of the Casco Bay Islands and a convenient summer destination, located just 10 miles from bustling Portland. Full of fine old houses, 25 miles of winding scenic roads, and one of the best hidden beaches in New England, it has the flavor and feel of an elegant summer resort town. The island’s sole hotel, the Chebeague Island Inn, sits perched on the top of a hill with a cozy great room and the kind of huge wraparound porch you’ll dream about long after your vacation has ended.Getting to Chebeague Island:Chebeague Transportation CompanyCasco Bay Lines, and Portland Water Taxi.
Squirrel Island
Photo Credit : Aimee Tucker

Squirrel Island | Boothbay Harbor

Quiet and decidedly un-touristy, Squirrel Island is a lovely day-trip destination for those who like to unplug. Located three miles from Boothbay Harbor, the island (from above, it supposedly looks like a squirrel holding an acorn) is Maine’s oldest summer colony, and measures just a mile long and barely a half mile wide. Run by the Squirrel Island Association since the 1870s, many of the hundred or so summer cottages on Squirrel Island now belong to fifth- and sixth-generation owners. There are no hotels. For visitors, five miles of paved sidewalks encourage strolling (cars and bikes are forbidden) and island daydreaming. Pop into the post office, library, and canteen for an authentic glimpse of island life.Getting to Squirrel Island: The Novelty mailboat from Balmy Days Cruisesin Boothbay Harbor.
Carver’s Harbor in Vinalhaven, Maine.
Photo Credit : Kindra Clineff

Vinalhaven Island | Penobscot Bay

Home to the state’s largest year-round island community and a sizable summer population of regulars and visitors, crescent-shaped Vinalhaven Island is surprisingly relaxed, with few cars and even fewer lodging options (the waterfront motel Tidewater is your best bet). Here on Maine’s largest offshore island, refreshing swimming quarries, a picnic-perfect nature preserve, and one of the world’s largest lobster fleets helped earn Vinalhaven a spot on Yankee’s 2016 list of the best hidden places in New England for a laid-back escape. We also recommend a stop at Greet’s Eats food truck for a lobster roll, noted for its generous portions in the 2017 Yankee summer feature, “The Great Lobster Roll Adventure.”Getting to Vinalhaven Island: The Maine State Ferry from Rockland.
Gull Cove on Monhegan Island
Enjoy the sweeping view from Gull Cove on Monhegan Island.
Photo Credit : Winky Lewis

Monhegan Island | Outer Islands

Located 12 miles off the coast, Monhegan Island has a natural beauty that makes it a popular day-trip destination. Enjoy stunning scenery, hiking trails to the high cliffs with panoramic views, an 1850 lighthouse (now a museum), and thriving art galleries. There are no cars on Monhegan, so come prepared for walking. A handful of comfortable inns and casual eateries serving up chowder, lobster rolls, sandwiches, baked goods, and ice cream encourage longer visits. Getting to Monhegan Island: The Monhegan Boat Line ferry from Port Clyde, or Balmy Days Cruisesfrom Boothbay Harbor.
Thurston’s Lobster Pound on Mount Desert Island.
Photo Credit : Amy Traverso

Mount Desert Island

We often refer to Mount Desert Island as the ultimate Maine “bucket list” island, and it’s not hard to see why. With 108 square miles of rocky coastline, towering mountains, teeming woodlands, and all the scenic trimmings of Acadia National Park, Mount Desert is a nature lover’s dream. Prefer shopping and strolling? The bustling hub of Bar Harbor, with its many restaurants, B&Bs, and tourist-friendly shops, guarantees the Mount Desert experience offers something for everyone. Don’t miss Thurston’s Lobster Pound for a lobster roll, another highlight from the 2017 Yankee feature “The Great Lobster Roll Adventure.” Perched above Bass Harbor at the base of the island, with its signature wall of buoys, this classic lobster shack (and the tasty roll itself) are two of Mount Desert Island’s top Instagram ops. Getting to Mount Desert Island: No ferry necessary — Route 3 offers drivers instant access.  Which Maine islands would you add to the list?