Out There: Boston Solo Travel Blog

Thor Skoe

7 days ago

4 min read

A Week in Boston

I went to Boston for work and this whole trip ended up turning into a Boston solo travel blog in real time, built around lobster rolls, American history, and me wandering the city with a camera.

Historic Boston building with American flag flying on the roof under a clear sky
Small brown bird perched on a metal table in downtown Boston
Group paddling under a Boston bridge wearing orange life vests on calm water
Docked yacht with American flag near Boston Harbor
Penguins standing on rocks beside water at the New England Aquarium
Brown bird resting on a perforated metal chair in a Boston park
Outdoor market scene in Boston with people walking among vendor tents
Penguins gathered on rocky ledge at the New England Aquarium exhibit
"Close‑up of a penguin standing upright on a rock at the New England Aquarium"

Boston Solo Travel Blog: Work Trip Turned Adventure

I flew into Boston on Monday to visit Perrone. Solid visit. Then I hopped a bus to Hartford to see the Rosadinis. After that I went down to New Haven to visit Matt Fryer. We had Sally’s pizza. It was dope. End of review.

I took a late bus back to Boston on Thursday night. That was supposed to be the start of the vacation part of the trip. Then Jen’s flight got canceled Friday morning and the couples weekend instantly became a Thor‑only weekend.

I had to check out of my hotel and get to The Dagny, but I was flustered, hungry, and still working. Somewhere in the chaos I ended up outside Union Oyster. It was 11 a.m. I was starving. I asked myself if that was too early for a beer and a lobster roll. The answer was yes, but I did it anyway. The Sam Adams Red Brick and the Maine roll slapped so hard that it reset my whole day.

Then I realized the hotel reservation was under Jen’s name because I booked it with her flight. So I needed her to call the hotel so I could check in. Not my finest logistical moment.

Friday night I went to The Barking Crab for a Connecticut roll and a few more Red Bricks. Shout out to the doorman for the recommendation. I walked the Greenway and went to bed early like a responsible adult who had eaten too much seafood.

Saturday on the Freedom Trail

Saturday I woke up early, grabbed coffee, tied my shoes, and headed to Boston Common to start the Freedom Trail. I had my camera and headphones and was ready to nerd out on history.

I sat at the Frog Pond and called my parents while the fog burned off. Turns out I was sitting on the same bench they sat on years ago while my brother and I played in the pond. That was a cool moment.

The Freedom Trail was awesome. I met a couple from Minnesota at the Granary Burying Ground. I saw “Ruckus” at the Old South Meeting House. I stood at the site of the Boston Massacre. All these old buildings sitting next to modern skyscrapers made the whole thing feel like time was layered on top of itself.

Lunch at Quincy Market was pizza, a Guinness pour that was legitimately perfect, and another Red Brick. I stopped at the Old North Church and visited the crypt where Major John Pitcairn is buried. Wild that a British officer who died fighting the colonists is buried in a church tied to the revolution.

Then came the long walk to Bunker Hill and the USS Constitution Museum. If I ever do this again I am taking public transport. By the time I got to Bunker Hill I was tired of being outside. The Constitution was great though. I am a sucker for boats.

Sunday: Improv Day

Sunday was supposed to be Jen’s day. Mass at the Basilica. Art museums. All things I just didn’t want to do alone. So I had to improvise.

I went to the Boston Tea Party Museum and Abigail’s Tea Room. On the way I bought a cup of tea so I could dump it into the harbor. Every American should do that once. Plus I promised my friends I would. I called my mom for her birthday and we talked for an hour while I tasted the teas that had been tossed into the harbor.

After that I went to James Hook for another Maine roll. At this point I was fully committed to Team Maine Roll. Connecticut had no chance.

I spent the afternoon at the aquarium. The penguins were awesome. The sea lions were insane. I watched two shows and could have watched ten more. It was a slow, easy day. I even went back to the hotel for a nap before dinner.

The Cheers Bar Detour That Was Not Actually Cheers

Everyone told me I had to see the Cheers bar while I was in Boston. So I started walking across the Common to go get my picture there. Halfway across the park I noticed a massive crowd. Not a few hundred people. More like fifteen thousand. And a stage. And lights. And speakers. I had no idea what was going on.

Turns out I had accidentally walked straight into Jaylen Brown’s goodbye party. The mayor was there. Lil Jon was there. A$AP Ferg was there. A dozen other artists were performing. It was wild. I was just trying to go see the Cheers bar and ended up in the middle of a Celtics farewell concert. Boston is a strange place in the best way.

A City Full of Solo Travelers

One thing I noticed all weekend was how many solo travelers there were. People eating alone, walking alone, taking photos alone, doing the same thing I was doing. It made the city feel safe in a way I didn’t expect. Boston is busy, but it never felt overwhelming. It felt like a place where you can be on your own and still feel comfortable.

Closing Thoughts

The trip didn’t go the way I planned, but it ended up being exactly what I needed. I got good work done. I saw companies I care about. I ate my body weight in lobster rolls. I walked through the birthplace of the American Revolution. I dumped tea into a harbor. I watched sea lions do backflips. I accidentally crashed Jaylen Brown’s goodbye party. And I learned that Boston is one of those cities where you can be alone without feeling lonely.

I’ll go back someday. Hopefully with Jen next time. But even as a solo trip, it was a good one.