Island Hopping in Casco Bay

  • A sunny day on Casco Bay.

  • Duckpin bowling at Great Diamond Island Community Center.

  • Capt. John at Casco Bay Adventures.

  • Kevin and Polly Wentworth of Chebeague Island Water Taxi with their children, Olivia, left, and Alden.

  • The signature blueberry cocktail from the Lobby Bar + Cafe at the Inn at Diamond Cove.

The gracious surroundings of a luxury hotel are home base for a weekend of exploring Great Diamond and Chebeague Islands.


My husband, Erik, and I are Mainers and love being on or near the water, so we’re thrilled to begin our weekend adventure on Casco Bay. We start with a quick trip on the Casco Bay Lines ferry heading to Great Diamond Island (GDI, as the locals call it). As we depart the Portland waterfront on a busy Friday night, we take a few deep breaths and feel the summer sea breeze wash away the stresses from our busy day, recognizing again how fortunate we are to live here.

GDI is a short trip from Portland, but it feels like you are miles away in an oasis of peace and tranquility. As we step onto the dock, we hear nothing but the gentle lapping of the water on the rocky beach and fall easily into Maine island mode. We are greeted by the friendly staff of the Inn at Diamond Cove, where we are staying for the next few nights. They escort us to the inn by golf cart, and we get checked in. Our room is spectacular—a luxury suite, which offers all the comforts of home, including a fully equipped kitchen, a living room with fireplace, hardwood floors, custom furnishings, and a spacious walk-in shower in the bath. The private balcony is a great spot for us to kick back with glasses of wine. We decide to have dinner in the Lobby Bar + Cafe, which is in a beautiful garden area—the perfect setting for a relaxing evening. We start with a light appetizer of tri-colored chips and house-made salsa fresco. We are hungry enough to order a second appetizer and ask for the lobster bruschetta, which is melt-in-your-mouth divine. Lobster is the theme for the evening as we both order our entrees: his a juicy filet topped with lobster and mine a buttery halibut filet on a bed of lobster risotto. I’m not sure how we manage to fit in dessert, but the menu is too hard to resist. While waiting for our salted caramel gelato, we sip creamy cappuccinos and wonder how we will ever be hungry again.


We rise early to take in the sights, sounds, and stillness of island life. A walk around the grounds gives us the opportunity to see some of the community of Diamond Cove and say hello to the locals as they start their days with coffees on beautiful front porches bedecked with American flags and rocking chairs. After a quick breakfast we head off on our first adventure of the day. We meet up with Beth Sanders, a volunteer for the Fort McKinley Museum, who will spend the next few hours showing us around Diamond Cove and Fort McKinley. The island was originally the location of a U.S. Army coastal defense base, formed in the 1890s to protect Portland Harbor and Casco Bay. Fort McKinley, named after the president, was the home of hundreds of soldiers housed in barracks and officers’ quarters throughout the island. The Inn at Diamond Cove now occupies one of those barracks and most of the buildings remain, having been restored and turned into private single-family homes or duplexes. Most of the batteries are heavily overgrown and on private property. However, it is clear that the community values the history of the fort and takes great pride in preserving it.


Casco Bay has so many islands to explore, and there is only so much time in one day. We decide to hop over to Chebeague Island Inn for lunch, calling on Kevin Wentworth, owner of Chebeague Island Water Taxi, to pick us up for the 20-minute cruise through Casco Bay. His 31-foot recreational fishing boat, the Result, is the perfect way to get out on the water for the afternoon. Arriving on Chebeague, we make our way to the front porch of the inn for lunch, pausing to take in the view of inviting wicker chairs arranged strategically on the shaded porch overlooking the bay. Set high on a hill, the inn has the understated feel of the quiet island life it represents. We are soon seated at a table on the dining side of the outdoor porch. Continuing with our lobster theme, I order the traditional Maine lobster roll and Erik gets the fish ’n chips, along with refreshing glasses of prosecco, before meeting up with our water taxi and heading back to Diamond Cove.


Diamond’s Edge Restaurant is situated right on the water with breathtaking views of Diamond Cove. We are seated on the lawn, poised perfectly for the evening’s sunset. The sky fills with shades of pink, orange, and purple as we enjoy our last evening on the island. The cuisine is unique, beautifully displayed, and so delicious. Chef Josh Hambrick makes an appearance at our table and we are delighted to meet him. Our evening ends with a quiet 10-minute walk back to the inn, where we join a few guests at the cozy firepit by the pool for one last beverage before turning in.



Before we leave this beautiful sanctuary, we order room service for breakfast and linger on our balcony while we listen to the morning songs of the birds and breathe in the seaside air before our departure. We have arranged for Casco Bay Adventures to take us back to the mainland and preview some of the charter adventures they offer during the summer months. Capt. John greets us at the docks with his energetic smile and quick wit, and I earn my unofficial Junior Captain’s license, when John let me takeover the wheelhouse for a bit.

While the boat trip was the perfect end to our 36 hours on Casco Bay, as we step onto the mainland, we admit that we need more time to explore. This brief Maine island experience left us eager for our next adventure and grateful for the peace and beauty that is so close to home.


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