Portland Travel Diary

I went on a girls trip with my best friends from college to Portland, Maine! Today’s post will be my travel diary from the trip back in mid-July. Click here for my Portland Outfit Diary. After college, my friends and I ended up in different states and scattered on both coasts, but we managed to make all our vacation schedules match up for a road trip. What sparked our trip was actually Ingrid Nilsen’s video with her friends to Portland, Maine, and we thought it was the perfect idea for our first post-graduation trip together. It was so much fun, so read on to see what we did!


We spent the majority of the first day driving to Portland. Joyce and Anny drove up from Delaware to meet Michelle and I in New Jersey, then we picked up Wendy in Boston and straight to Maine! When I say “we drove”, I really meant to say Joyce drove haha. It took about eight hours to get from Delaware to Maine, with some stops for picking up people and getting fast food. I mean, you kind of have to eat fast food when you’re on a road trip, that’s part of the fun! We stayed at an AirBnB not too far from Downtown Portland and it was an amaaazing place. It was actually a barn that the owner turned into a house. Definitely one of the best AirBnB experiences ever. (If you read my Ottawa Travel Diary you probably know about the horrible AirBnB experience.)

Our second day together was our first day in Portland, and we rented a boat from Portland Boat Rental to spend the day on the Casco Bay. On the way to Casco Bay, we stopped by The Holy Donut for some (a dozen) donuts to eat on the boat. These donuts are made with potato flour, so they are a tad bit healthier!

When we got to the boat rental, the owner taught us how to drive the boat. It was all fairly self-explanatory, and four out of five of us ended up driving the boat at some point during the day. All we had to do was turn the engine on and steer – the best part is that there is pretty much nothing for you to crash into haha. We hooked our boat onto one of the floating balls (sorry, I don’t remember the boating terms anymore) and ate our donuts while we relaxed. It felt so good to not have anything to worry about, which was definitely much needed for all of us.

There are over 300 islands in Casco Bay, but the two main ones that are closest are Great Diamond Island and Peaks Island. We docked at Great Diamond Island (sidenote: some islands have docking fees), and went on a walk to explore. The majority of the island was residential, but we found an open space and snapped some group photos. I definitely recommend renting a boat for a day just to relax and experience the boat life!



Day two in Portland was for the famous lighthouses and Downtown Portland, but before that, we had to fuel ourselves with delicious food. We had gone to Whole Foods the previous night to pick up some pancake mix and other goodies, and had a family breakfast! We hiked around Portland Head Light and then decided to take out the kite to try it out. I’d like to think that we were pretty good and that we did not fail our childhood selves, but there was a kid and a father who were definitely wayy better than we were. Nevertheless, it was fun to fly the kite around after a good fifteen years.

After our #flashbackfriday, we drove to Downtown Portland for dinner at Duck Fat and to pick up some blueberry pie from Two Fat Cats. Maine is known for its blueberries, so you will literally see blueberry everything – blueberry pie, blueberry jam, blueberry beer. There are a lot of boutique shops in Downtown Portland, and an ice cream place where I had coconut ice cream for the first time and it was sooo delicious! We spent the rest of the night at the AirBnB eating blueberry pie and just hanging out because who knows when the next time we will have all five of us together (hopefully soon!).


This girls trip was much needed and it was so nice to get away from work : ) It brought back college memories and we have all grown so much from just one year of living in the real world. I will forever remember that day when we went to Phipps Conservatory and then cooked dinner at Morewood : ) Thanks for sticking with me since orientation week and I can’t wait for our next adventure <3


For all my outfit details, head over to my Portland Outfit Diary. If you liked this post, please check out my Colorado Travel Diary and come back on Wednesday for my Montreal Travel Diary! Thank you so much for stopping by : )


1 Comment

  1. August 14, 2017 / 10:35 PM

    Looks like it was such a fun trip!! So cool that you stayed in a barn as an Airbnb haha!

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