My Trip to Boston, May 2026
I wished my trip to Boston was much more eventful. The majority of my trip was sight-seeing. To be fair, sight-seeing does rank high on my itinerary when I visit a new city. But, I usually try to squeeze in at least one heart-pounding activity (such as the zip-lining I did in Vegas). But there were hardly any thrilling activities to partake in Boston to begin with. And, Boston is definitely a town for foodies but my strict diet precludes me from enjoying good food (I’m gluten and dairy-free so no lobster rolls for me!). But, I did what I could in the few days I was there.
I grew up within walking distance of a landscaped parkway so, Commonwealth Avenue had nostalgic value. I couldn’t walk too long, though. The day before my I arrived, I was very dehydrated…
Commonwealth Avenue
I love immersing myself in a new city and feeling like a local so, I usually try to take some form of public transportation. Later on in the day, I learned the bus schedules and made a trip to MIT’s chapel. It’s a bit of an architectural wonder. While there, I met a young Chinese student whose parents were with him and had just attended his graduation from Yale (I was quite flattered when he asked if I had just graduated from college myself)…
Chapel at MIT
Chapel at MIT
I took the bus back across the river and found myself close to Boston University’s campus…
Boston’s brownstones are marvelous…
I hopped on the train and took it a few stops to Boston Common Park for some more walking. I’m embarrassed to have been seen doing such tourist-y things but, to my credit, it was by pure accident that I ran into Cheers…
Cheers is one of my favorite sitcoms so, it was nice to see the original Cheers sign. For the record (and I’m sure you’ll agree), the best part of the series was with Kirstie Alley…
A short while later, I found myself in quaint Beacon Hill…
I always try for at least one dinner outing during my trips. This time, it was a tapas bar at the seaport…
It was a lovely, warm night so I took a stroll along the seaport before heading back to my hotel…
The next day was the highlight of my trip: sailing! … Okay, it was actually underwhelming and I was hoping the waters would be rough like the scene in The Truman Show when Christof tried to turn over Truman’s boat… It was nothing like that (I told you, I need a thrill!). Instead, I sat on very calm waters and freezing to death because Boston can still be very cool in May…
On my last full day in Boston, I ate at Copley Square, did a little shopping, and visited the Boston Public Library. It’s a lovely, cavernous, old building. I visited their famed study hall with the banker’s lamp shades (growing up, my dad had at least 3 original banker’s lamps. When I finally got a place of my own, I begged him for one of his lamps. Instead of telling me he didn’t want to give up any of his antiques, he bought me a replica - a lamp with a cheap plastic base made to look like polished brass)…
Boston Public Library
Bates Hall, Boston Public Library
Boston Public Library courtyard
Thus ended my last day in Boston. I was relieved to just get back to my room and re-pack for my flight the next morning. I’d used up a lot of energy walking. On my next trip to Boston, I will definitely walk the Freedom Trail, sample some very fresh fish, and get on a speed boat. If you’re a lover of Boston, do send your suggestions!