When we were planning our wedding, Jake and I went back and forth about whether or not to take a honeymoon. Ultimately we decided on Portland, Maine because it was on my list of places to travel to during fall. We also knew that when the honeymoon came along, we would be happy to have some vacation time after all the wedding planning. We booked our trip in July with our wedding being in September, and admittedly we forgot we had even booked the trip until right before walking down the aisle.
Is that what you’re meant to think about right before getting married? HA!
our portland | maine honeymoon
For the trip, we kept things simple staying at an Airbnb just outside of downtown. Our Airbnb was a cute, third-story loft and our host was so sweet, providing some snacks and a local brew when we arrived. The host also encouraged composting and offered reusable grocery bags to borrow during our stay. We also rented a car to get around and had little trouble with traffic or parking.
Portland has been the first place I’ve traveled to that is reminds me of home. Coming home to people in Minnesota and the relaxed feel in our state are two of the things that keep me here. In Maine, everyone was so nice and caring, and enjoyed small talk – similar to Minnesotans.
While the honeymoon ended up being amazing, it didn’t start out very good. Our flight out was cancelled at 8PM the night before – our flight was at 6AM. We were re-booked on three flights (rather than two) that didn’t get us into Portland until nearly 8PM which made us lose a day.
We started our day bright and early to makeup for the lost day of travel. We grabbed breakfast at a local favorite Becky’s Diner. This cute diner was right on the bay just outside of Downtown.
After breakfast we walked along the bay into downtown just as stores started to open. On this Sunday, there was a cruiseliner that was in port so there were a lot of tourists walking about and vendors setup with local gifts for sale.
On top of the list of things to do while in Maine, was visiting the Portland Head Light Lighthouse which is the most photographed lighthouse in the United States. I don’t think we could have asked for a more perfect fall day for this adventure. It was sunny, mid-60s, very windy with all the colors changing around us. We also took a walk in one of the city’s parks!
Next on top of the list of things to do was visiting Shipyard. Pumpkinhead was the brew we used to drink at our fall parties many years back so visiting the brew house was sentimental to us. My best friend (and Maid of Honor at our wedding) is a brewer and had also requested us visit while in Portland. We grabbed a table and a flight, including their Smashed Pumpkin which I enjoyed more than their famous Pumpkinhead.
For dinner, we went all out with Maine lobster at the Old Port Tavern which is located in the basement of the historic Mariners Church Building. Since we were celebrating, we ordered a bottle of champagne and some delicious hot crab dip. I had the Casco Bay Haddock while Jake enjoyed the Maine Lobster special.
We woke up on Monday with no solid plans other than to enjoy the day. The weather was a little crisper than the day before, but still sunny. We started with breakfast at the Other Side Diner, which as the name suggests is on the other side of Portland. The diner was tucked away in a little neighborhood near the bay, and had the sweetest staff. Not to mention the local food was delicious and
After breakfast we drove out of town to Freeport which is home to many outlet stores and gives you small town vibes. After walking the town, we headed to Bradbury Mountain State Park for a hike. This park was the reason I had always wanted to visit Maine during fall. We hiked up the mountain and at the peak were all the fall colors and forest.
For our last dinner of the honeymoon, we ate at David’s Restaurant which is owned and run by a Portland native. We loved this restaurant – the atmosphere, food, drinks, service. All of it was amazing. If you’re in the area and want to treat yourself to a nice dinner, I highly recommend checking this place out. We had to grab some ice cream after diner (obviously!) so we walked to Beal’s Old Fashioned Ice Cream parlor, where they had a pumpkin flavor I couldn’t pass on.
We checked out of our Airbnb early Tuesday to enjoy the last few hours we had in Portland. We grabbed another diner breakfast at
After breakfast, we headed to the Holy Donut which is famous for their handmade, potato donuts. They have two locations, and when we were in Downtown on Sunday the line was wrapped around the block. We only waited a few minutes at their suburb location, which was well worth it. I grabbed the fresh lemon flavor before heading to the airport.
After arriving home, I realized that our honeymoon was casual, relaxed and simple. And it was just what we needed. Planning a wedding and doing (nearly) all it ourselves was an amazing experience because we got exactly what we wanted. At the same time, we were busy all summer and were due for some much needed R&R. I wouldn’t change of a thing of our honeymoon.
If you looking for a vacation where you can relax, enjoy some good food and want to go some where you can relate to the people, then you’ll love Portland. There’s so much to do no matter if you’re a nature lover, city person or history buff. And if you can swing a trip during the fall, the colors and weather will not disappoint.