If truth be told, we were having second thoughts about Chebeague Island Inn – a classic New England retreat off the coast of Portland, Maine – before we’d even stepped through the front door.

Just getting there is a journey in itself: a 90-minute drive north of Boston to a nondescript parking lot in Cumberland, Maine, followed by a seven-mile ride in a school bus to Cousins Island, a 15-minute ferry ride across Casco Bay to Chebeague Island and a quick transfer by minibus to the inn.

Inside, the inn’s great room, with its stone fireplace and rustic furnishings, did little to change our first impressions.

The dark wood-paneled bar was empty, and our compact bedroom and bathroom – albeit decked out with crisp white cotton sheets and towels – had the understated charm of an old family summer cottage.

Time for a Bloody Mary and lunch, we decided. Then suddenly, everything changed. As guests filled the garden-front dining room, we noticed everyone was chatting like old friends.

Children mingled happily between tables, and the  staff seemed to know everyone by name.

As lunch progressed – with light-as-air homemade biscuits, a sensational lobster roll and lip-smacking flourless chocolate torte – we started to settle into the rhythm of the place.

“Is this your first visit?” enquired a diner at the next table. “Our family has been coming here for years, and  we wouldn’t have it any other way.”

It didn’t take us long to find out why. After a game of chess in the great room, a snooze on the wide terrace overlooking Casco Bay and a few rounds of cornhole in the garden, we were more than ready for sunset cocktails and another superb culinary experience by the inn’s talented executive chef Matt Ginn.

That night, lulled by a cool breeze blowing through  our bedroom window and the silence of coastal Maine, we slept soundly.

Originally built as a hotel in 1880, then rebuilt in 1920 following a major fire, this landmark three-story, Greek Revival-style inn has offered warm and genuine hospitality for more than a century.

Perched atop a hill and nestled in two-and-a-half acres of grounds sloping down to a golf course and Casco Bay, the 21-room inn was restored in 2004 and relaunched in 2010 under the new ownership of mother-son hoteliers Gerri and Casey Prentice.

They listened carefully to feedback from the inn’s loyal and long-term clientele and, while making some much-needed improvements, decided to retain its innate “unplugged” ambience (there are no TVs or phones in guest rooms, but Wi-Fi is available throughout).

Hotel activities include croquet, badminton and other lawn games, while the island offers beaches, swimming, tennis, golf, clamming, sailing, deep-sea fishing, kayaking and island excursions.

We enjoyed a wonderful morning cycling around the island – Chebeague is a Native American name pronounced “shuh-beeg” and translating to Island of Many Springs – rekindling happy memories of carefree summers.

The best decision the Prentices made was hiring chef Ginn, who has transformed the inn into something of a culinary destination, featuring seasonal menus and a relaxed Sunday Jazz brunch.

We left the island for an evening to dine at Evo, Ginn’s own restaurant in downtown Portland. The food and service were first-rate and well worth the ferry ride back to the mainland (there’s also a scenic one-hour ferry from downtown Portland that stops at some of Casco Bay’s other islands).

The inn is open May through October and makes for a thoroughly relaxed and casual weekend escape or a longer summer vacation.

When it was time for us to leave, we’d pretty much fallen for the place, teaching us never to judge a book     by its cover. 


For more information, visit chebeagueislandinn.com and evoportland.com.


Image Credits: Photo by Jeffrey Stevensen.