This was our third trip to Maine, but the first time focusing solely on the city of Portland, and doing the whole thing without a car. Previously, we visited the coastal areas around Bar Harbor and Acadia National Park, as well as the inland areas of Baxter State Park and the Katahdin Woods and Waters National Monument. Portland, ME has always been on our shortlist of cities we would like to explore; we just didn’t expect it to be in winter!
Portland is a beautiful city to simply walk around and enjoy the sights of a New England waterfront port town. Every day, we tried to soak in as many of these unique sights as we could, visiting all the unique offerings we could fit into a weekend that Portland had to offer.
Transportation:
Our travel dates were Thursday, January 26th – Monday, January 30th, 2023. Our journey began as usual in Washington DC. We had a Delta companion pass (through our credit card churning efforts) that was set to expire on the last day of January 2023, so this was a perfect use for it. We flew out of Washington’s DCA airport after work and connected through New York’s JFK for both our outbound and return flights. We were lucky enough to have time to utilize our Priority Pass (which we also obtained for free through churning) to grab a free dinner and beer at DCA, and some snacks and a drink at JFK while we waited.
Upon arriving in Portland, we chose to take a taxi to our hotel as it was immediately available and priced the same ($18.00 + tip) as an Uber/Lyft. I would note that there was also a city bus option that looked convenient if you were arriving earlier in the day. At this point, you probably notice that there is no rental car listed here, which is one reason we settled on Portland, ME for this trip. We realized it was not necessary to have a car to explore the town, and it was compact enough to explore on foot.
Lodging:
We stayed at the Hilton Garden Inn Portland Waterfront and secured a great winter rate of $118.00 + taxes per night. Upon arrival, we were lucky enough to get a room with a water view of the harbor across the street. I did “pick my room” ahead of time on the Hilton app and did some light research to find the side of the hotel not facing other buildings. Still, I did not realize it would be a water view, so I highly recommend using the Hilton app ahead of time whenever you are booking a room, just to see what is available.
Activities:
Thursday – The day we arrived did not leave much time for exploration as it was already around 10 pm when we got to our hotel. However, we did make the most of our time by walking around the few blocks near our hotel, popping into a place that was playing live music and grabbing a quick beer before settling in for the night.
Friday – Today was forecasted to be sunny all afternoon, so we planned a sightseeing boat ride for noon. The Casco Bay Lines company, operating out of the marina across the street from our hotel, has a variety of water taxi and sightseeing options to pick from. As it was winter, there were fewer options, making it easy for us to decide what we wanted to do. We chose what I thought was the most unique way to see Portland and the surrounding area from the water – the mailboat run.
This was a working boat that runs a circuit route from downtown, carrying passengers, mail, and freight to the islands throughout the bay.
In preparation for the 3.5-hour boat ride, we stopped at a deli and grabbed some sandwiches to eat onboard. The crew encourages passengers to bring food and beverages. There’s a store across the street from Casco Bay Lines that sells local beer and wine, which you can also bring onboard. We made about seven stops at different islands. It was interesting watching all the deliveries. Most of the packages were USPS mail and Amazon packages, but some stops had bulk freight like building supplies, air conditioners, etc. Between all the stops, you pass by lighthouses, natural scenery, wildlife, and sweeping views of Portland. We were pleasantly surprised to have such a large boat mostly to ourselves on this sunny winter day.
We can confidently say that if you have time for one attraction, pick the most interesting boat ride that fits your itinerary and do that – it was a blast!
After our boat ride, we took some time to stop by a few restaurants to grab dinner and try local beers. To finish the night off, we stopped by Arcadia, which had about 50 arcade games, most of which were retro and unique games we hadn’t seen elsewhere.
Saturday – We spent most of this day walking around the downtown area, visiting shops, and taking a long walk on the waterfront promenade trail. We visited the highest spot in the city, tried our favorite beer (Maine Lunch) of the trip, and saw the train that runs seasonally for tourists along the water. We highly recommend taking the time to stroll along the waterfront as the trail is easy to walk and stretches for miles.
After dinner, we decided to check out the local hockey game that was only a few short blocks away. Portland was playing Norfolk this night, and the arena was mostly full, and the crowd was energetic. We loved stopping in for an impromptu local hockey game as a way to finish off the night and feel like a local for a day.
Sunday – We started this day by sleeping in, as I was well on my way to catching a cold and was feeling pretty groggy. After we rested and ate breakfast at our hotel, we walked a few miles on the promenade again and eventually found our way downtown to finish the night off at a bar where we played darts.
Overall – The highlights of this trip were the boat ride, for which we highly recommend getting out on the water in some way to see the town. We also really enjoyed going to a local hockey game on a day when the local team won, and the crowd was enthusiastic. Otherwise, Portland is simply a beautiful town to walk around in and visit the shops and eateries that line the streets and waterways.
Leave a reply