3 Days in Portland Maine

Portland Maine was nothing like what I expected. I was looking forward to a quiet area with bustling beaches, okay…I was looking for a place similar to York Maine. I was so wrong when it came to Portland.

Portland is a City, the moment I got there I realized how much this city means for the economy. Don’t get me wrong, Portland was a really cool city, I just wanted to make sure I reiterate that when you go to Portland, you will be going to a city not a beach vacation. But because of that, it means you have some really cool things you can do. Here’s a 3 day itinerary for anyone going to Portland Maine.

Day 1

Try to arrive early so that you have 3 full days in Portland because trust me, there’s enough to do. On your way there, consider going to Kittery for the outlets, I mean, why not? We booked an Airbnb rather than a hotel and it was the best decision. It was in a quiet area and close to the city. If you stop at Kittery, you’ll probably only end up going downtown for dinner, trust me, it’s worth it. Walk around the city a bit and see what there is to offer — both from food and activities. There are a ton of options and I’ll get to that in a bit.

Day 2

Wake up early and head to the beach, but be prepared, the beach will be expensive. It was over $30 dollars for us to park at Scarborough beach, I was shocked, luckily it was being split by 4 people. Scarborough Beach is about 20 mins from the city. If you like waves, body surfing and boogie-boarding (or even surfing) this is the beach for you.

After getting all the sun you need, head back down to the city and go to Duckfat for an late lunch and early dinner. The food was beyond amazing. You can’t live without the fries once you have it and even though it’s not fish, the panini’s were out of this world. You might have to wait a bit to get in, but don’t worry, East Ender has some epic drinks and a lovely bar to hang out in before your seat is ready.

East Ender Bar

After dinner, head to the Pier to go on a boat cruise, specifically a sunset cruise which starts around 6:30PM in the summer. It was SO much fun and probably one of my favorite things about Portland. That’s partly because it reminded me the most of being on a beach vacation and we learned a lot about the history of Portland and it’s surrounding islands.

Did I mention that I got to see lighthouses? I love lighthouses, it’s what I love the most about the Ocean.

Day 3

Speaking of Lighthouses, Day 3 was another relaxing day but this time to Cape Elizabeth. While our friends went on a whale watch, we walked around Cape Elizabeth and Fort Williams Park.

Fort Williams Park is gorgeous, there are so many random places to walk around and see. We went pretty early too so we didn’t end up having a lot of people around while we walked away to look at everything. The first place we went to was Goddard Mansion, or to be honest, a ruin now. It was so sad to see that this once amazing Mansion that had such promise not too long ago. I feel like there are so many of these structures in the United States, it’s one of the reason I appreciate Europe so much.

After Goddard Mansion, we started walking up toward old military structures, something that we loved, because again, we love history. Plus, the view of the City and lighthouses were a lovely area to just sit around and relax.

After there, start your way toward Portland Head Lighthouse where you will walk through a gorgeous garden, where we saw multiple engagement photos going on. But honestly, if you were to go there, you would know exactly why people would want their pictures taken.

After walking through the garden, you’ll start walking toward the main attraction and trust me it’s the main attraction. My goodness, the Portland Head Lighthouse is gorgeous.

Seeing it in real life made me realize why it’s one of the most photographic lighthouses in the world. It was the most relaxing morning we could have had there. So of course, afterwards, we had to do what Portland Maine is known for — brewery tours!

We had so much fun trying all the different beers in Portland Maine, there were so many different varieties that it was hard to pick just one. In the afternoon we were able to go to multiple all within walking distance of each other. My favorite was Shipyard because honestly, they had a beer for everyone. I can’t wait to tell you the epic beer trail we made, it’s perfect for craft beer lovers. Look for that post soon!

Portland Maine had it’s ups and downs, there were some parts of it that I loved like Cape Elizabeth but what I had really wanted was a beach vacation, Portland doesn’t necessarily offer that. I’m not saying to not go there but I think I would always pick York Maine (a little south) over Portland if we went that way again.

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