A small tropical styled bistro on Great Diamond Island that features seafood dishes like mussels escabeche, seared scallops, and lobster arancini. Stop in here for some great food and fun drinks!

Reservations strongly recommended.

Diamond Cove is home to 6 secluded and private beaches. Enjoy spending time relaxing at any of them!

Housed in the former quartermaster's storehouse overlooking Diamond Cove, Diamonds Edge restaurant offers waterfront dining for a relaxing lunch or dinner featuring local seafood and New England Favorites, and amazing views!

Guests can choose to dine in the dining room or on the deck or lawn if the weather is right.

Reservations strongly recommended.

The island has miles of trails and island roads to walk or bike. Bikes are available for rental at the Inn.

Diamond Cove has 2 heated pools. The Cabana Bar + Firepit located at the Inn is the ideal place to swim, sip, relax and wind down the day.

Diamond Cove is located on what was previously Fort McKinley military base that was built during America's Gilded Age. Army structures are scattered over the island and have been restored, mostly to homes with wonderful historic detail and character. Prior to being a military base Diamond Cove was a famous artists' retreat where American literary greats such as Henry Wadsworth Longfellow and Harriet Beecher Stowe spent time. If history is your thing, definitely check it out!

The island has a turn of the century bowling alley featuring duckpin bowling, ping pong, pool tables and classic arcade games. Stop in to play a frame!

The store offers grocery items, ice cream, pizza, fresh sandwiches, lobster rolls, beer & wine, live or steamed lobsters, creative dinner specials and events throughout the summer.

The indoor basketball court located in the islands former Post Exchange is the perfect place to dribble a ball around. The rec center for Inn at Diamond Cove is also located in this building.

Tennis and Pickleball courts are available for those that would like to play a match!

Visit Portland Head Light, a historic lighthouse in Cape Elizabeth, Maine. The light station sits on a headland at the entrance of the primary shipping channel into Portland Harbor, which is within Casco Bay in the Gulf of Maine. Stop here for gorgeous views and great photo ops!

Standard is one of our favorites! Stop into this family owned bakery that has a diverse array of daily breads, sweets and breakfast pastries. We recommend the prosciutto & asiago croissant or a morning bun!

Bug Light Park is a popular destination for picnicking, boating, kite flying and salt water fishing. This cute little lighthouse is great for a good view and a relaxing walk!

A Maine classic! Stop in for some Maine potato donuts made from scratch daily.

Visit the only caisson-style light station in the United States that visitors can walk to. It is located on the breakwater at Southern Maine Community College in South Portland. You can walk all the way out on the rocks and get up close to the lighthouse!

One of our favorite dinner spots in Portland! This rustic spot has an open wood fired grill with exceptional service. They change their menu every day based on what is in season so you are always getting the freshest ingredients.

Reservation highly recommended!

Head to a Portland Sea Dogs game to watch a minor league baseball team that is affiliated with the Boston Red Sox. The Sea Dogs have a game on Friday September 5th or Sunday September 7th for those that are in town and interested!

This 2 mile trail is great for a harbor-side stroll. It begins in downtown Portland and connects to the Back Cove Trail and Bayside Trail. Take a walk for beautiful views and enjoy the food trucks along the way!

Stop in to Otto for a quick, extra large slice of pizza!

DiMillos is a great spot for spectacular views of the Portland Harbor! Stop by this floating restaurant that was formerly a New York car ferry for some great seafood.

Beals famous old fashioned ice cream is crafted in small batches in a wide variety of flavors. Swing in for a delicious treat!

One of our favorite Portland drink spots! Fun fact, Mak worked here in high school and part of college. Portland Regency Garden Café is open for lunch, dinner, cocktails and desserts. Open as warm weather permits. Located in the heart of Portland it is the perfect spot for a casual patio drink.

Great coffee and pastries with a good ambiance. Get your coffee to-go or sit and enjoy!

Family owned, craft beer brewery located in the Old Port. Small bites and pizza also available here!

Located right on the water, this is a great spot to grab a flatbread pizza with a good drink. Flatbread is located right by the ferry port if you are waiting for a pickup to the island.

This restaurant that once started as a food cart is a good place for a tasty lobster roll. Stop in to try a a Maine classic or burgers and corndogs too!

Located in the heart of Portland, The Crooked Mile is a fantastic place to stop for a good breakfast sandwich and a yummy coffee.

If you're in the mood for a vintage inspired cocktail bar this is the spot for you! Great drinks and small bites found here.

One of our favorites in Portland! Cute atmosphere with internationally inspired small plates with local and seasonal ingredients.

Freeport is about a 30 minute drive outside of Portland. Great for shopping!

Acadia is about 3 hours away from Portland. If you come to Maine early or are staying after the wedding it is definitely a place you should check out!