Islands Near Portland Maine - Tempting Islands of Casco Bay

The Peaks Island Ferry in Casco Bay

“It’s kind of a special feeling, when you’re out on the sea alone, staring at the full moon like a lover.” The Little River Band Must have explored Casco Bay’s lusty islands when they wrote “Cool Change,” way back.

If you closed your eyes tightly, thought of your loftiest wishes, filled your cheeks with a huge breath – and splayed out those wishes with the force of a gale as though wishes were islands – they’d land in a smattering all over Casco Bay, Maine. This veritable Gulf of Maine inlet displays wildly-varying sized and shaped clusters of land, some more inhabited than others. These islands lie in the “greater” Portland area:

Chebeague, Cliff, Great Diamond, Little Diamond, Long Island and Peaks Island.

Map Of Islands Near Portland

The map below shows the locations of the Casco Bay islands mentioned in this post:

This section of Casco Bay encapsulates coastal Maine. Sort of a microcosm of the Maine coast all within a brief jaunt in any direction. Ogle a couple of lighthouses, far-out forts entrenched in centuries of history and rooftop turf. Secretly bet on a little white sailboat engaged in a distant race. Notice the unparalleled pride of the tugs guiding behemoth barges. See lobster boats zip around leisure vessels with an almost instinctive sense of one another’s harmonious purpose on the bay. Applaud the occasional, daring harbor seal poking out her head for a heroic breath in the middle of it all.

Fire in the hole! A ferry blast sounds out routinely on the leaving at the Maine State Pier off Commercial Street. The Portland coastline is a blend of well-worn yet vibrant and working waterfront activity, lined with oil tanks, a world-class kiting kite flying park, a Wyland Whaling Wall mural, high-end condos, nautical shops and boutiques, clusters of yachts, and more restaurants per capita than in any other U.S. city, second only to San Francisco. The ferry runs day and night, year-round, is incredibly affordable, and well worth checking out, here.

Long Island is a romantic hideaway, edged with beaches, trails, and a sense of semi-privacy, relative to some other islands. Day tripping? Perfect. Bring a backpack with some healthy nibs and H20; stop along the trail to notice your reflection in the crystal water buffing the pointed rocks with each new tide. Of Maine’s 4,000 total islands, this is one of only 15 bearing year-round residents. Naturally, the quiet community swells with visitors in the summer, but Long Island maintains a cool, calm, command of its heritage. The Town of Long Island reaches out to include the neighboring islands of Cow, Long, Overset, Vaill, and a portion of Little Chebeague.

Great Diamond Island may be just a 20-minute sail from mainland Maine, she is the grand dame of “heyday” isles, preserving the festive feel visitors had while dining on the oceanside lawn as though tipping a timeless hat to the sea. Weddings and larger events happen unforgettably, at the Inn at Diamond Cove, which began in the 1800s. Now, luxurious condos and rooms are available here. Additional dining and lodging opportunities blend with resident cottages and houses, where visitors and locals share this memorable spot in the sweeping bay. Bring a bike, a towel, a lunch, and a mindset for good old-fashioned fun.

Little Diamond Island holds pinkies with Great Diamond Island, connected by a sandbar that is visible at low tide. Go see it.

Chebeague Island, how you brave against Time and crashing waves, yet always retain your beauty. A stone’s throw off the Phippsburg coast, the island hunches just beyond where the summertime-populated Popham Beach stretches into the abyss, winding on alone for miles. The Slow Bell Café weathers the storms along with its stalwart neighbors; do check ahead for additional hours at this 5-star Yelp darling. Tough to feel more like Scotland in New England than by spending a day on “the links” golfing that offers excellence at every vista: https://chebeagueislandgolf.com/. The charming, 3X5 mile isle is a destination for pleasant walks amid the hush of history. Sandy beachlines and casual biking rival bonfires and tennis for your attention. A “night at the inn” is a mouse click away . . . Here, on an island filled with love and lore, time stands still in the truest sense.

Peaks Island is the kid at the front and center of the class, hand in the air, waving you in. Just minutes from Portland, it’s a whirlwind of activity. Grab an ice cream or a bite at one of the waterfront eateries with a million-dollar view. Rent a cart or a bike and explore the ins and outs of the busy island. Paddle awhile. Studios, funky museums, and an elegant library-(check here for safety restrictions) all welcome artistic and literary curiosity. If you venture away from the throngs of folks coming on and off the ferry, you’ll find smashing breakers, stately homes, and active neighbors. Mystical cairns bedeck the more free and wild backside of the island. Oh well, if you miss this ferry, there’s always the next. Hotels, inns, and cottages scratch the itch to stay for more than just a day. . .

Cliff Island, the smallest year-round island in this region, proudly protects its commitment to conservation. With unpaved roads, sheltered acreage, and eight miles of shoreline magic, harbor-lovers have plenty to explore here. Children leap into the sea (and some daring adults as well), where it looks like a glance back into the days of Robinson Crusoe. Serrated cliffs and deep emerald pools – with nothing in between — but adventurous people jumping midair. A café, store, and wellness center are among the well-kept community buildings, one-room schoolhouse and active historical society here, where no more than about 50 people live year-round. How enticing, and worthy of protecting.

What’s more fun than riding the waves over to a remote isle for a classic in-ground lobster bake or clam feed with a bunch of co-workers or others peeps? Once the boat docks, the hustle-bustle happens with the seaweed and the smoke and the steaming potatoes, corn and lobsters, eventually leading to a classic one-pot meal desired the world over.

Legend has had it that 365 islands bedeck the bay, hence the nickname, “The Calendar Islands.” But time revealed that closer to 750 islands lie in this 1000-mile watershed, teeming with life and history, with the tempestuous North Atlantic tickling its toes.

Other ways to get around include several water taxis, which are easy to find online. Or, experience the Mailboat Run. This authentic, working boat sails passengers – as well as cargo and mail – to each of these islands, all year long. Plan ahead, and no matter the weather when you depart, assume it will be colder once you’re offshore.