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4 Islands to Visit Off the Coast of Portland, Maine

woman holding hat on ferry ride
Written by Suzy Guese

As Maine’s biggest city, Portland can seem downright busy, even though it’s small in size. The city is loaded with historic charm by way of cobblestone streets and 19th-century architecture, and is well known for its hip restaurants and craft breweries. Portland can feel perhaps a bit too cosmopolitan if you’re looking for a more laid-back Maine experience. However, just beyond the city, you can reach a number of islands that lend that quiet, calm, and of course, that fresh lobster that Maine is so famous for. Get away from it all by island-hopping to these four favorites.

Peaks Island

Hop aboard a ferry and in 20 minutes you can reach Peaks Island. Home to nearly 1,000 year-round residents, the island is enticing for its history and proximity to Portland. Offering up commanding views of the city and the ocean as well, Peaks Island was known in the late 1800s as Maine’s very own Coney Island, complete with hotels, theaters, shops, and an amusement park. The island even served as an important outpost during World War II. In terms of activity, the island includes museums to explore, from the wacky Umbrella Cover Museum to the history exhibits at the Fifth Maine Museum. The island also encourages more leisurely pursuits like popping into its many art galleries, shops, and restaurants along the appropriately named Island Avenue. And nature lovers will appreciate the island’s many beaches like Sandy Beach and Cairn Beach.

Great Diamond Island

Great Diamond Island

Just a 25-minute ferry ride from Portland, Great Diamond Island presents a picture-perfect Maine island. Home to hiking trails and spots to picnic, the island is mostly a private island community. You can pretend you’re a part of the community living here by visiting the waterside restaurant or arranging for a trip on some of Great Diamond’s private lands. As no gas-powered vehicles are allowed, Great Diamond Island is decidedly pure and unhurried. It’s no wonder that big names like Henry Wadsworth Longfellow or Harriet Beecher Stowe used to frequent the island.

Chebeague Island

Chebeague Island has been enticing families for generations, so much so that it has only around 350 year-round residents but welcomes a whopping 1,600 visitors come summertime. The largest island in Casco Bay measures 5 miles long and 1.5 miles wide, but it’s not too big for its island britches by any means. Settled by New England colonists in the 1700s, Chebeague Island was once an important center for shipbuilding. Today, summer brings more activity, but the island still has just a handful of businesses and places to eat. The island is all about leisure these days, where you can go a few rounds at the 1920s Great Chebeague Golf Club, marvel at all the old homes on a stroll, or park yourself on a beach like Indian Point Beach. The ferry from Portland takes 60 to 90 minutes one way.

You may also like: A Guide to the Historical Side of Portland, Maine

Bailey Island

Bailey Island, Maine

If you tend to turn green just thinking about getting on a boat, there’s still an island within reach of Portland for you that doesn’t require a ferry ride. About 50 miles from town, you can hop on a few bridges to Bailey Island. Part of the 216 miles of coastline in the Harpswell Neck, Bailey Island sits proudly as the outermost island in Casco Bay. It remains an ideal island for engaging in popular Maine pastimes, like feasting on lobster at one of the island’s praised restaurants or frequenting an art gallery or two, or merely watching the Atlantic Ocean crash onto the shore.

What’s your favorite Maine island? Share your pick with us in the comments below!

About the author

Suzy Guese

Suzy Guese is a travel writer from Denver, Colorado. She caught the travel bug after taking her very first flight at just three months old—she was headed for Disney World—and has been a total travel junkie ever since. From family car trips across North America to stints abroad in Europe, Suzy travels the globe with her redheaded temperament in search of sarcasm, stories, and travel tips to share with anyone willing to listen. She blogs about her travels at

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