Best Islands in Casco Bay

“If once you’ve slept on an island…you’ll never be quite the same.” So goes the idyllic book by Rachel Field… Nowhere is that more true than on an island in Maine…in summer…

It’s magical being surrounded by water, your arrival and departure solely reliant on a boat, far removed from the traffic, hustle and bustle of mainland living… it’s surprising how life slows, how so-called “necessities” melt away and life’s real “niceties” emerge… quiet, calm, natural, just the sound and smell of the sea.

Casco Bay in Portland is dotted with beautiful islands, over 200, some more inhabited than others… like Peaks and Long Island being the most populated, and easily reached by Casco Bay Lines ferry system from Portland.

Here are three special Maine islands that come to mind, very unique from one another, well worth discovering …

Chebeague Island is a step back in time, although its Maine’s newest town – Chebeague became independent from Cumberland in 2007. This beautiful wooded island with several sand beaches is home to a hearty community of 350 islanders, year-rounders.

Chebeague – pronounced “sha-beeg”, is the largest island of the Calendar Islands… a reference to the number of islands equaling the days in the year in this region (slight hyperbole but a fun anecdote). Chebeague is actually comprised of 17 islands, the “Big” island is 3 mile long by 1 mile wide. Settlers in the 1740’s farmed and lived here, lobsters were so abundant they used them for fertilizer, not food. By the 1900’s Great Chebeague had five hotels, now there’s just one – the lovely 1880 Chebeague Island Inn atop a sweeping lawn that leads to the western shore and view of mainland, and Yankee power plant.

Spend the night at Chebeague Island Inn, you owe your soul the experience! Arrive by ferry or your own boat and be whisked up the hill in the courtesy van to this historic charming hotel. The cozy fireplace living rooms lead to a gracious veranda with sea views. Take bikes to the East Shore beach, or explore the two roads – North & South – past the Historical Society and Maritime Museum, the Slow Bell Café, the island grocery store, community center and school.

Back at Chebeague Inn, cocktails are served on the easy breezy porch, followed by the acclaimed Chef’s delicious dinner – lobster, local mussels, duck, in the classic dining room or out on the lawn – our preference. Sunsets do not dissapoint here from the west-facing hillcrest overlooking the bay. Sleeping at the Inn -with your ocean view windows open, the light white drapes fluttering in the sea breeze – is perfection.

Great Diamond Island is a gem in the heart of Casco Bay, just a mile from Portland. This historic island has remnants of 1890’s Fort McKinley – the country’s coastal defense system built to protect Portland’s Harbor. The Inn at Diamond Cove is in the beautifully renovated old brick army barracks.

Casco Bay Ferry delivers you to Diamond Island’s protected “Cocktail Cove” and you check in at Diamonds’ Edge restaurant before being carted up the hill to the Inn – golf carts and bikes are the preferred transpo around the 1.3 acres island – which is mostly private for the 100 residents and hotel guests. We  rode the elevator from the airy lobby to our modern room with a lovely balcony, note: views from the hotel are of the beautiful “parade grounds” but not the ocean from the  high forested point.

As guests of Inn at Diamond Cove, we could hop on a complimentary bike or stroll to the old artillery spots – from the Spanish American War, visit the beach or sit by the hotel pool, hot tub and Cabana bar. There’s croquet, tennis, even indoor bowling and basketball. After a day boating Casco Bay and exploring the island, our balcony was a delightful spot to rest and relax before walking down to the Cove and waterfront for a wonderful seafood dinner at Diamond’s Edge. We passed the Crown Jewel, another popular spot for diners that came by ferry or more fortunate like us spending the night. Our ideal island-hopping day concluded with a dip in the cool pool back at the Hotel, then nightcaps by the fire pit.

Eagle Island is for the explorer, truly. This dramatic island in Harpswell, eastern Casco Bay, is a Maine historic site, and former home to Admiral Robert E. Perry who ventured to the North Pole in 1909. You can tour his family’s 1904 summer home, complete with artifacts from his bold expedition, even a Polar Bear. Bring a picnic, and enjoy the ocean views from this prominent point, admission is $5-6, plus your sightseeing ferry ride to the island. Overnights on Eagle Island are not permitted, so allow yourself at least an hour to tour the island, home and museum.

If you love Casco Bay, and sleeping on islands, surrounded by the sea, continue your tour of the Maine coast onwards, down east, towards Sebasco, or picturesque Boothbay Harbor – staying out on the dramatic peninsula at Ocean Point Inn, on Southport Island at Newagen Inn or the classic summer campy-style Linekin Bay Resort.

Monhegan Inn view in MaineFor real remote island life, venture out to sea to rustic Monhegan Island and lodge at the rustic Charles House or Trailing Yew. Hiking around the impressive ocean cliffs, seeing Monhegan Lightouse, the weathered granite shores and sand beaches is exhilarating. Witnessing how the islanders live, so humble and resourceful, is a lesson in independance, minimalism, and heartiness. Visiting Monhegan, even for a day by ferry, must be on your Maine Bucket List! Better to stay the night and feel the freedom, the solitude and the sea.

Cadillac Mountain viewPenobscot Bay – midcoast Maine – is loaded with beautiful islands and the scenic sailboat loaded harbors of Camden, Rockport, Lincolnville, and Rockland.

Finally, Mount Desert Island, home to Acadia National Park and Bar Harbor is Maine’s most magnificent island for touring, hiking, biking, boat rides to lighthouses, and seeing the sunrise first in the country atop Cadillac Mountain.

See our Guide to Touring the Coast, and Boating in Maineplan your vacation in #Vacationland… The way life should be…see our Guide to Visiting Maine!

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Copyright and photography – VisitMaine.net, 2019

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