The “Original” Portland

Portland, Maine was the perfect weekend getaway. We would’ve loved to stay for all three days, but with work we were only able to spend an afternoon and morning there. Fortunately, it’s just the right size for a little excursion like that too!

Where to Stay

We decided to go to Portland kind of last minute so we didn’t get a chance to stay at any of the unique hotels (which I definitely want to try next time) that are in abundance in Portland. But we did stay at the Holiday Inn-Portland by the Bay, which was in an excellent location! We were just a short 10 minute walk from the main downtown area. Right across the street from the Portland Museum of Art and catty-corner from Little Tap House, good if you don’t want to go far for a bite to eat. Everywhere we went during our stay, was within walking distance which made it a very laid back and enjoyable time!

Where to Dine


I was able to grab an oh-so famous Holy Donut. I paired the chocolate sea salt donut with an almond coconut coffee. It was so good and located right in the heart of the downtown where there are many people-watching opportunities.

The Holy Donut in Portland, Maine | Things to do in Portland, Maine.


We originally were planning on going to the highly recommended Eventide Oyster Company, but unfortunately, they don’t take reservations. This was kind of a turn off at first, but we thought we’d go ahead and give it a try. There was over an hour wait so we just walked around from there and stumbled upon East Ender that seated us right away. It’s an adorably quaint restaurant with amazing food. My husband ordered the braised pork shoulder that came with a side of cheesy grits, cippolini agrodocle, and charred scallions. The pork was so tender, it just fell apart. I ordered the ricotta gnocchi which was cooked with north spore mushroom argue. Our waitress described the gnocchi as clouds that melt in your mouth, and she was not wrong. The portions were the perfect size too, which I love. No one wants to waste good food or walk around holding a box of leftovers that you’ll inevitably leave in the hotel fridge. All in all, a wonderful experience!


From East Ender, we walked 5 minutes to the main downtown area and stopped in at Gelato Fiasco. It was popular and thus pretty busy, but they were still very efficient and there was hardly a wait at all. The staff was friendly and helpful when asked to explain all the interesting flavors. My husband ended up getting a mix of cookie dough and cookies and cream, while I got pistachio. They were both delicious, and since I did try a few samples, I can tell you if you’re a chocolate lover, their dark chocolate and the chocolate sea salt were both amazing!


The next morning, we walked about 15 minutes to Bayside American Cafe. We got there at about 9:15 and there was a small wait, but it wasn’t a big deal because you could get a mug of coffee and sit and talk until you were called. (I will warn you to not come too late because when we were leaving, there were a lot of people waiting; it’s a popular place!) I was glad we were seated upstairs because there was more light, and it was very pleasant. My husband and I both wanted eggs benedict, but since they had an extensive “benny” menu,  we each got something different. He ordered the bistro steak benedict and I got the Maine lobster benedict; so good! We always want something sweet with our savory for breakfast, so we also got one cinnamon bun pancake to split, and boy were we stuffed but very satisfied!

What To Do


There are lots of shops along Exchange Street. After my snack at The Holy Donut, I wandered into a few shops that run up and down the street. There are lots of cute boutiques that made it pleasant even if you’re just window-shopping.

Portland Head Light

Probably the best part of our little excursion was the lighthouse! Built in 1791 and still in operation, it is the most photographed lighthouse in the country. After we visited, we could see why.  It was absolutely beautiful, and you could actually walk up to it. There’s also a museum you can tour in the former keeper’s house. The lighthouse is in Fort Williams Park, which is also charming. If I lived in Portland, I would come here every day to walk or have a picnic. There were many different viewpoints from which you could take in all the beauty. We ventured along a path and then climbed down and across some rocks to get a more picturesque view of the lighthouse which was fun (but if you’re planning on attempting this, make sure you wear shoes you’re confident in). They also had a few cute snack trucks which had coffee and ice cream, if you’re feeling sweet! I definitely recommend adding this to your must-do list when visiting Portland.

What I Wore

I bought these sandals for all our summer travels, and they have served me well. I wanted sandals that were good for long distance, but that I could also wear with all my dresses. They were recommended by many people as good walking shoes, and they did not disappoint! I even wore them on the day we climbed all over those rocks. My husband had Nike tennis shoes on, and I kept up with him step by step in my sandals! Cute and super comfy, which is hard to find.

Things we didn’t get to do but I recommend

On our way to the Portland Head Light, we went through South Portland which was so cute! I really wish we’d had time to stop and look around. So if you’re headed to the lighthouse, I would recommend carving out an extra half hour to stop in a few shops or just slow down to take in the pretty houses. Here’s a few places I saw that I really wanted to stop in and check out:

What about you? Have you been to Portland yet? Was this guide helpful? I’d love to hear about your adventures or any suggestions you may have!



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