Portland, Maine

Monday – 9/11

We woke up in Nantucket and quickly got ready for the big day ahead. We got delicious bagels and pastries for the road at The Bean, and then made some very impulsive clothing purchases, and got on the ferry back to Hyannis. The ferry ride was mostly uneventful, there was a cat in a carrier meowing the whole time.

Once docked we got a ride to Enterprise from a very friendly guy, and then we waited at Enterprise for them to bring our car over for awhile. We met an older couple (at least in their late 60’s) traveling from Phoenix. I asked how long they had been waiting, and they said almost an hour, and she said the employees said the hurricane in Florida was impacting their car stock. I said that sounded like a line of bull, and the woman told me I was too young to be that cynical.

We got in our rental car and drove straight to Chick-Fil-A. It was our first experience and it was so yummy! The sandwiches and milkshakes were way better than Shake Shack. We then set our on our drive for Portland, ME. We made a playlist on Spotify of the music we listened to on this road trip! Lots of Joseph! Listen to it here!

Once we got to Portland we found our BNB, the Inn on Carleton, and it was absolutely stunning. This was our favorite hotel stay during our whole trip. Leo and his wife Patricia were the owners and they are outstanding hosts. Leo gave us a map and told us his favorite places for dinner. We dropped our bags and set our on foot for Congress Street. We had dinner at Local 188, Ryan got house paella and I got a simple salad and a side of their house meatballs. It was so good! Back at the BNB I took a bath and started reading “The Children” by Ann Leary, and Ryan watched a lot of Cops.

In the evening, we picked out a DVD to watch from the bed and breakfast’s stash. We watched P.S. I Love You.

Tuesday – 9/12

We woke up to a beautiful sit down breakfast at the BNB, we were served fruit with yogurt and homemade granola, and then cinnamon french toast with a side of sausage. Again, the Inn on Carleton was absolutely stunning and the service was excellent.

We drove over to the Old Port and checked in at the Regency Hotel for our couples massage. This was Ryan’s first ever spa experience. We used the co-ed hot tub and sauna before, and then got massages together from two wonderful masseuses. Ryan felt very indifferent about the whole experience, didn’t love it but didn’t hate it. I think it was one of the best massages I’ve ever had!

After our relaxing spa experience, we walked through the Old Port. We went to Andy’s for lunch, where Ryan got a lobster roll, and I got meatloaf. It was a very authentic old Portland bar. We then shopped around Old Port, and went on to the Portland Observatory. We climbed 130 steps to get to the top, and saw sweeping views of Portland and some really big cruise ships that were docked. We then drove to the Portland Art Museum, where we got to see the McLellan Mansion, as well as some beautiful modern art.

By this point in the day it was really hot and we were tired. We went to Gelato Fiasco and had some of the best gelato I’ve had since being in Italy. It was so good. We went back to the BNB and took a short nap before meeting up with Marci.

Marci is an old family friend of mine. She moved to Portland Oregon when she was in her mid 20’s, I was probably about 7 years old. She met my parents and they quickly took her under their wing. She worked at Nobbys, lived in our attic for a bit (who hasn’t?), and has a beloved sun conure named CJ that lived at our house the whole time she was in Portland. She was born and raised in Portland Maine, and I was so excited to see her again!

Marci picked us up in her convertible Mini Cooper, and we went to a “secret bar” she knew about in Old Port. We got to catch up on everything and it was so fun! We even FaceTimed my parents so she could say hi. Then she took us on a driving tour around all of Portland, we got to see amazing neighborhoods with huge houses and beautiful areas where she goes kayaking. Then she drove us all the way to Old Orchard, a cute little beach town south of Portland. It was a beautiful sunset. We didn’t get as much time with Marci as we’d like, so we know we’ll be back to visit and explore more of the area.

Marci had to be at work at 8PM, so she dropped us off around 7:30 and we went to a really great pizza place near our BNB. It was a very hip and trendy spot, with lots of locals. It was recommended to us by multiple people, and it didn’t disappoint.

Wednesday – 9/13

We got up early and had breakfast at the BNB again. That morning we had fruit again, and delicious eggs benedict. We checked out, hit Dunkin’ Donuts for coffee (Ryan is now obsessed with it???), and drove to Mackworth Island.

I’ve got to give some history on Mackworth Island here. When I was young I 100% believed in fairies, I regularly left notes and houses for them in my backyard, and I totally believed they were hanging around me all the time, sprinkling magic everywhere. Marci was around for this period of time, and she would always tell me about an Island in Maine that was like a whole fairy city, where people go to make fairy houses, and the fairies live there even when it snows. I remember this so clearly, I swore I would someday go to this Island. And so there we were, on Mackworth Island, the fairy Island! It was a dream come true.

Mackworth Island is about 100 acres, and has a trail that loops the Island, it’s about 1.25 miles. The Island also houses Governor Baxter School for the Deaf and Hard of Hearing, which is really cool. There are amazing views of Casco Bay and Portland, and there are so many squirrels and chipmunks everywhere. There was an amazing swing overlooking the water, and the trails were really nicely kept. There were fairy houses everywhere and 7 year old me was in heaven! About halfway through the hike I heard a rustle in the leaves and looked to my left and saw a decent sized garden snake, and nearly ran the rest of the way back to the car. But snake or no snake, we absolutely loved Mackworth Island and would definitely go back.

We then drove to the Victoria House, a beautiful mansion built in the 1860’s. We love to look at old mansions and see how fancy people used to live. It was beautiful and I would recommend it to anyone in Portland.

Just a few blocks away was a restaurant we wanted to check out but had been closed when we tried on Tuesday evening. It’s called Bao Bao and it’s a dumpling house created by some famous chef. It was so good. It was so. good. I’m so glad we went. It was one of the top 5 best meals of the trip. Ryan enjoyed it, but I honestly haven’t really stopped thinking about the pork scallion dumplings.

We then drove to Ogunquit and saw Marginal Way, and then continued down 1A to Portsmouth, New Hampshire!

Our final thoughts on Portland:

Portland was so great! We couldn’t believe how many young people were there, it really is a growing city. Rent is starting to skyrocket as more people move in, but it’s still significantly less than Portland, Oregon or San Francisco. It was so great to see an old friend, and Ryan got to meet Marci for the first time. As she drove us around she kept saying “If you were staying longer you could do that…” and so we will definitely be back! It was a beautiful and calm little town on the water. We absolutely loved the BnB we stayed at, and we would definitely stay there again. Can’t wait to go back!