A pristine and tranquil island surrounded by Casco Bay, Great Diamond Island is one of 200 plus islands referred to as the “Calendar Islands” — where you can supposedly explore a new island each day of the year. This peaceful and secluded island is the perfect spot for luxuriating in a secluded, romantic weekend getaway. Dotted with small beaches, parks, and homes for approximately 100 year-round residents, the charming island is perfect for contemplative walks, romantic beach sunsets, and quiet conversations.
The laid-back vibe of the island is enhanced by the minimal amount of cars. There are a few commercial vehicles, but in general, cars are not permitted on the island. The back-to-nature experience is enjoyed on foot, bicycle, or golf cart adding to the charm and elevated camp-like nature that permeates the island lifestyle.
Great Diamond Island was part of Fort McKinley’s coast defense system protecting Casco Bay and Portland Harbor; the central green with encircling buildings reflects its military history. You will find the historic Inn At Diamond Cove and charming cottages ringing the green space.
Note: Some information in this piece was obtained during a sponsored press trip, but all recommendations are my own.
Inn At Diamond Cove
The Inn at Diamond Cove, formerly the army barracks, dominates one end of the central green. This is your home for the duration of your island getaway. The beautiful building has been carefully restored to retain its grand original style.
The wide-sweeping porch overlooking central green is an oasis just off your spacious room; perfect for idling away the afternoon with a great book or a pre-dinner glass of wine while enjoying the sounds of nature.
The inn is a member of the Historic Hotels of America, the official program of the National Trust for Historic Preservation. Requirements to be inducted into the program include: the hotel must be at least 50 years old, designated by the U.S. Secretary of the Interior as a National Historic Landmark or listed in or eligible for listing in the National Register of Historic Places, and recognized as having historic significance.
Pro Tip: When you disembark the ferry, you will likely encounter a line of golf carts and a few vehicles. The Inn at Diamond Cove offers a van shuttle to carry you up the hill to the inn.
Casco Bay Lines
Great Diamond Island is accessible by the Casco Bay Lines ferry. The ferry services several islands along the route, picking up and dropping off passengers, mail, and provisions. The ride time varies and takes about 30–45 minutes, but the beautiful coastal Maine scenery will hold your attention. You can feel a marked relaxation take hold as the ferry glides over the bay waters and the breeze cools your skin. Have your binoculars handy as you may spot a variety of coastal birds and wildlife along the journey.
As the ferry crew goes about their tasks, it is easy to gain an understanding of how much effort is involved in procuring food, clothing, and everyday items. As you watch the dock hands march bins of goods off the boat and load up other pallets waiting on the dock, it imparts a sense of hardiness mainlanders take for granted.
You can explore some of the other Calendar Islands by hopping on and off the ferry.
Pro Tip: Other methods of transportation to the island include private boats or water shuttles.
Pleasant Cove Beach
Hitting the beach tends to be at the top of most vacation lists and you will find a few good options on the island. Little enclaves of beaches (mostly sand and pebbles) are sprinkled around the island. Pleasant Cove Beach is one such spot, perfect for a nearly secluded beach day. Pack a picnic lunch and your favorite beach read for a day of peaceful relaxation along the shoreline.
Pro Tip: Keep in mind, the water in Maine is cold — very cold! All you need is a quick dip to cool down.
Fort McKinley Museum
The Fort McKinley Museum is open seasonally offering tours, historical exhibits, and other events throughout the summer months. The small museum building is located near the ferry dock.
Pro Tip: Advanced reservations to visit the museum are required.
A simple stroll down a dirt road will bring you up close and personal with some of Mother Nature’s beautiful gifts. Unplug and watch a family of deer grazing in the field, enjoy a picture-perfect view of Casco Bay, or get slightly lost in an old-growth forest. Take full advantage of the secluded island and seek out her quiet solitude.
Pro Tip: Carry your binoculars and camera. Be on the lookout for eagles, osprey, herons, and loons gliding past.
Diamond Cove Tennis Courts
Practice your serve and work up an appetite on the Diamond Cove Tennis Courts. Set in the natural beauty of the island, the courts are available for locals and island guests.
Fort McKinley Post Exchange
Fort McKinley Post Exchange, the former base Post Exchange, is now the island activity center. It is a perfect space to get out of the hot summer sun or hide out on a rainy day.
The large building houses a wealth of activities. A well-equipped fitness center is available if you need a little indoor workout. Weekly yoga classes are held in the spacious yoga room. There is the original indoor basketball court, game room, pool table, and other games to keep you occupied.
Most interesting is the refurbished pre-war-era duckpin bowling alley. Bowlers set the pins and then mow them down with a thunk of satisfaction. Even if you don’t bowl, you need to give this a try at least once.
Diamond Edge Restaurant
The Diamond Edge Restaurant is situated right on the marina with panoramic views of Casco Bay and Diamond Cove Marina. The seasonal restaurant offers a casual vibe and fabulous coastal cuisine.
For a classic Maine dinner, the traditional lobster bake with corn on the cob, Littleneck clams, Maine potatoes, and a nicely-sized lobster is the perfect plate to celebrate a Maine Coast vacation.
The Lobby Bar + Cafe
In a sweet, secluded courtyard adjacent to the Inn at Diamond Cove is The Lobby Bar + Cafe. It is a wonderful spot for a leisurely breakfast or quiet dinner. With only a few tables surrounded by lush plantings, the patio imparts an almost private ambiance.
The menu is filled with fresh ingredients for a light meal, served with a glass of wine. It is a wonderful way to end a day exploring Great Diamond Island.
Romantic Weekend Getaway
Great Diamond Island is the quintessential coastal Maine romantic weekend getaway. The secluded island is a secret paradise. Your stay at the Inn at Diamond Cove is just what you need for a private getaway where you can simply immerse yourself in the luxuriousness of relaxation. Guests return year after year to relish the peace and quiet of this unique Portland, Maine, vacation spot.
Pro Tip: The Inn at Diamond Cove, the Diamond Edge Restaurant, and other attractions are open for the summer season — May through September.