On our roadtrip we also drove down to Portland, Maine after Bar Harbor. My Bar Harbor guide is posted here. In Portland, Maine you’ll find a hub with cobblestone streets, local shops, and scenic working waterfront views. It was definitely more of a “city” feel as compared to Bar Harbor. Portland reminded me of Philadelphia in a way especially with the wide variety of restaurants. We were only in Portland for 2.5 days so we attempted to do a lot!
What we did:
Portland Schooner Co: Sunset Sail
On the website they have an option for a private or public tour. We scheduled the public sunset tour with is a two-hours Windjammer cruise on Casco Bay. You can pack a meal as well as beverages. We saw a couple of larger groups bring beers and soda in a cooler on board. The boats also have bathrooms on board but the way down is very steep. The sailboats are all wooden and listed on the National Register of Historic Places. The boat is also slightly interactive if you choose to volunteer to pull up the sail. We thought this was a wonderful experience and the crew was very professional.
Trolley Tour and Portland Head Light
We were tired at the end of our trip so we opted for a Trolley tour called the Portland City and Lighthouse Tour. The tour is about 1 hours and 45 minutes with an informative guide explaining the history of the city. The guide was fully narrated and engaging while we looped around all the spots of the downtown Portland area and to the final stop of the Portland Headlight.
Peaks Island with Golf Cart Rental
We took the ferry over to Peak’s Island and rented a golf cart for a total of 4 hours. You take a ferry over which takes about 15-20 minutes. You only need to buy a ferry ticket for the way there and then you just get on the ferry for the way back. Unfortunately we went at an awkward time as the ferry leaves at 12:45 PM or 2:45 PM from Peak’s Island so we were there for way too long. If you are looking for entertainment, this is not for you. We rented a golf cart for 2 hours, but one hour would have been fine. I would highly recommend making a golf cart reservation as they do sell out quite quickly. We went around the entire island in about 1 hour and just went around for a second time because we had time to waste. There is a small assortment of restaurants near the ferry stop so you can grab lunch there and an ice cream. Although the views are pretty, wouldn’t go back as I found it quite boring. It did remind me of just riding a golf cart around a deserted suburb.
Flight of Kombucha
There were numerous places to drink kombucha as well as breweries. I happen to love Kombucha so we ventured over to Root Wild where I was able to choose a flight of 4 different flavor options. If you really like a flavor you can order a bigger size or take some cans to go. I got the ginger, blueberry, and 2 rose flavors. I thought this was a really fun thing to do for tastings.
Old Port
We also stayed in Old Port so it was easy for us to get to and from the restaurants. This area has beautiful cobblestone streets, restaurants, bars, specialty stores, boutique shopping, and the fisherman docks as well. While walking around there are so many great restaurants to try along the way which I will note below. Commercial Street is a historic street that runs along the wharves of the harbor. The Old Port portion of the avenue runs roughly between the Casco Bay Ferry Lines and Becky’s Diner that is about a mile long. There are numerous tours available along Commercial Street, including the trolley tour I stated above.
What we ate:
Portland has made a name for itself as a foodie city. We weren’t there for long but the restaurants we tried were amazing. There are huge lists online for great places to go based upon the cuisine that you prefer.
Lenora: 10/10: This Mexican food was so flavorful and filling. We ordered the guacamole, mushroom dorados tacos, lobster tostada, elote, and the black bean tostada. I will say the portions are quite small so make sure you order enough. The food tasted so fresh and the dishes were creative.
Via Vecchia: 10/10: This eatery is a small plates Italian inspired restaurant inside a beautiful brick and ivy covered building. The restaurant is absolutely beautiful inside with a 20 seat bar surrounded by velvet booths. We ordered a lot of different items including kale caesar, shrimp alla griglia, zucchini, and risotto. I would highly recommend going here for dinner.
Eventide: 5/10: We got the “famous” lobster roll and it was not my favorite. The bun itself reminded me of a bao for some reason so the texture was very off. Also the roll was so small to my surprise. This place makes almost every list for the best lobster roll but maybe the other items are good.
Holy Donut: 8/10: I am a donut lover and this donut was an interesting spin on a donut. The owner after months of experimenting and taste testing with friends and family, she finally landed on a northern Maine recipe that includes riced potatoes. The donut has a very dense taste and didn’t taste overly sweet. They have so many interesting flavors and a selection of gluten free options.
Standard Baking Co.: 8/10: This bakery is family owned and operated that has been part of downtown Portland since 1995. The baked goods are prepared throughout the day in a stone deck oven. If you want an assortment of items making sure to get there when they open. I walked over about 15 minutes after they opened with about 15-20 people in front of me. I would highly recommend looking at the menu online before you go as I felt rushed at the register. We ordered the croissant, blueberry oat scone, and granola bar. I will say the granola bar was EXCELLENT. I’ve had better croissants and scones at other bakeries but I am sure they have plenty of other great options.
Where we wanted to eat: Duckfat: We really wanted to try the fries but every evening we went had a 45 minute to 1 hour wait.
Where we stayed:
Hyatt Place Old Port: The location was very ideal in Old Port so we were easily able to walk to most restaurants and activities. The hotel itself was clean but it’s very bare bones. Just be aware that service is not the priority at this hotel. The housekeeping just did “light service” on our room which meant they just dropped off towels with nothing else.
