Our 8th Anniversary: Portland, Maine

Thomas and I celebrated our 8th anniversary in Portland, Maine last weekend.

With everything going on in the world, it was nice to get away on a road trip and to enjoy eachothers’ company. I tried to spend as little time as possible on my phone, and to spend as much time as possible adventuring and living in the moment.

dancing beach anniversary

We left for Portland on Thursday. After a rainy drive up, we made it just in time for some dinner. We had drinks and dinner and a bar called Rosie’s. We ate at a picnic table on the cobblestone street. We were pleasantly surprised by a horse and dog who relaxed on the grass while their owner enjoyed dinner. I would recommend a Paloma from Rosie’s as it was strong and delicious for a decent price! We explored the downtown area by the harbor and headed back to the hotel.

On Friday, I walked over to Holy Donut for some delicious freshly-baked donuts. I picked them up for breakfast and brought them back to the hotel as Thomas had work. After breakfast, I relaxed and went on a nice 4 mile run/walk at a nearby trail. I picked up lunch for us, and after Thomas’ work day, it was time for exploring. We went to see the Portland Head Light and Bug Light before dinner at Flatbread Co. Seeing these lighthouses really brought me back to my solo road trip here a few years ago. To read more about that, click here. 

I would not recommend Flatbread Co. After calling for a reservation earlier in the day, we were instructed that they do not take them; however, we can request to be on the waitlist if we call back later. I called later and was told the waitlist was an hour long. With our names on the list, we assumed the wait would be an hour as discussed. Thomas and I had to wait 2 hours from the initial call and then about another hour for our 1 pizza to arrive to our table. 

We would not let that ruin our time! We enjoyed ice cream cones after, and had a lot of laughs.

ice cream Portland Maine

On Saturday, our 8 year anniversary, we went on an adventure to Peak’s Island. We boarded the ferry, rented bikes, and went exploring. After seeing the gorgeous coastline, we grabbed a beer and mermaid cocktail at a local lobster spot. We split a lobster roll, and raced to make the ferry.


We dined at Demilo’s that night, and really enjoyed our time. The views of the yachts (while dining on one) was lovely. I enjoyed a Paloma and another lobster roll, and Thomas tried the lobster BLT with a Maine beer. We had a really nice time.

After dinner, we went to the beach and just relaxed. We took some photos together, and to my surprise an instagram follower friend recognized me. We took a quick photo together…hope I look good in that one Tracy 😉

After some photos and enjoying the sunset, we went to a speakeasy bar in Portland for a drink and zeppoles to go.

On Sunday, we grabbed Holy Donut to go and road tripped back.


Overall, we had a great time together. It was nice to feel a sense of normalcy and enjoy each other’s company.


Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s