Yes, you can island hop in New England. There are so many harbor islands all along the coast. Portland, ME is home to seven major islands and dozens of smaller ones. On a recent trip to Portland, we left the mainland for one of the most unique New England getaways we’ve ever had! Read on to find out about our trip to Portland and Great Diamond Island!

Portland

We are huge fans of Portland; the food, the people and the scenery make for a convenient weekend escape. There is plenty to do! If you are lucky enough to visit in the summertime, you have to get out on the water. What is more New England than a 100-year-old schooner off the coast of Maine in June?

The Portland Schooner Company operates right from the Maine State Pier and offers daily sails all throughout the day. We took a midday sail and it was the perfect way to kick off the summer! We sailed on the Bagheera all around the Portland harbor and enjoyed the beautiful view of the city and the Head Light.

And after a breezy ride, we explored Portland’s famous food scene and lunched at Pan Mei Miyake.

Their ramen is not to be missed! All my ramen lovers need to add it to their list whenever they make it up to Maine! For more of my dining recommendations, see my other post about Portland. 

Where to Stay

Portland has a lively downtown. To be right in the middle of all the action, stay at Portland Harbor Hotel in the Old Port. Recently renovated, the rooms are airy and bright with a delightful nautical theme.

And the on property restaurant, Bluefin, just rolled out a new summer menu filled with locally-sourced seafood. The tuna tartare, lobster popovers and halibut are not to be missed!

If the weather is nice, they have a large patio which is truly an urban oasis as even many locals are not aware it exists!

Island Hopping

Once you have gotten your bearings in Portland and are itching to explore, head to the islands!  Great Diamond Island is the place to go! Formerly an Army base, this island is now a car-less escape from the hustle and bustle of daily life. As soon as you dock, you are greeted by staff from the Inn at Diamond Cove in golf carts ready to whisk you away.

The Inn at Diamond Cove is the only resort on the island.  It was formerly an army barracks as part of the military base erected at the turn of the 20th century. When the property was restored in anticipation of its 2015 opening, they paid close attention to the original character of the historic property.  There are many classic New England details that can be found throughout the hotel. And the rooms are modern and spacious!

A stay at the Inn at Diamond Cove can be whatever you want it to be, relaxing, active or a little of both! There is a fabulous pool, a nice patio, firepit, yoga studio and bikes that you can borrow.

Great Diamond has a few quintessentially beautiful Maine beaches, plenty of bike paths and tons hiking trails to explore!

After a day of exploring the island, you can come back to the hotel for a relaxing meal at their lovely lobby restaurant. Another seafood focused menu, the lobster rolls, crab cakes, lobster crostini and ahi tuna tacos are definitely worth a try!

But here the drinks are also the star! With freshmade ingredients, such as Maine Blueberry puree, a cocktail by the firepit is the way you’re going to want to unwind.

And when you wake up, you get to enjoy a simple, but satisfying breakfast in that fresh Maine air!

Back to Portland

From the time you land at Diamond Cove, to the time you leave you feel a weight lifted, the tranquility of the island washes over you like the Atlantic tides. But eventually we all have to get back to reality and when you do, you just hop on the ferry back to Portland and you can be on your way! But before you go, try to get out on a boat one last time to enjoy the sunset in the harbor. We were able to with a little help from TripAdvisor!

TripAdvisor makes it so simple to book experiences on the go! We booked a private boat ride in a historic lobster boat during sunset on our last night in Maine. Thanks to TripAdvisor we were able to compare options, read reviews and book instantly! It was the perfect way to end our trip to Maine!