If you’re planning a trip to Portland Maine and want a realistic plan that doesn’t leave you exhausted, here’s exactly what we did over four days. A good mix of food, coastal towns and just enough wandering to feel like a proper trip without trying to do too much.
Day One: Arrival
We landed in Boston around midday and made the two hour drive up to Portland, arriving in the late afternoon with just enough time to settle in before dinner. We stayed at the Hilton Garden Inn Portland, which turned out to be the perfect location, walking distance to almost everything. Unless we were driving out of the city for the day we didn’t touch the car once. We started with Eventide Oyster Co. and Duck Fat, both well worth it but both also quite busy. We didn’t have reservations ahead of time, so if you’re in the same boat I’d recommend making one of these your first stop in the afternoon rather than the evening. The weekend dinner lines are no joke! Full thoughts on both, along with the rest of our favourite meals, are in my Portland restaurants guide.
Day Two: Oysters and Coastal Towns
We started the morning at Tandem Bakery, and if you go you have to try the biscuit with butter and strawberry jam. Simple but one of the best bites of the whole trip! From there we headed about an hour outside the city for our Glidden Point Oyster Farm tour at 11:30am, one of the real highlights of the trip, you can read the full experience here. From the farm we drove to Damariscotta, walked the main area and browsed the shops for 30 to 45 minutes before lunch at The Lobster Haul. From there we continued on to Boothbay Harbor, sat by the water for a while, checked out a few more shops and drove back into Portland for the evening.
Day Three: Lighthouses and Lobster Rolls
Breakfast at Standard Baking is non negotiable, get the cinnamon roll while you’re there. From there we drove to Portland Head Lighthouse, which is considered the most photographed lighthouse in the entire United States, and once you see it in person you understand why. We spent the morning walking the grounds before grabbing a lobster roll from Bite Into Maine, possibly the most scenic lunch spot on this whole list. From there we drove down to Two Lights State Park for a walk along the coast, then continued on to Kennebunkport for the afternoon. We came back into Portland for dinner at The Shop by Island Oysters to close out the day.
Day Four: Peaks Island and the City
Our last full day started with the ferry over to Peaks Island. You can rent a golf cart but we chose to walk instead, making our way to the other side of the island along a beautiful stretch of coastline. Back in Portland we spent the afternoon wandering the city, stopping at Harbor Fish Market and working through a few of the shops from my Portland shopping guide. We ended the trip with a 5:30pm dinner at Central Provisions, which is worth booking in advance.
Day Five: Departure
A short morning before our flight out of Boston at 4pm, just enough time for one last walk if you’re staying close to the city.
Four days was the right amount of time to feel like we’d actually experienced Portland without rushing through it. If you’re planning your own trip I hope this gives you a solid starting point to build from!
