How to Spend 48 Hours in Boston

When I was little, we used to drive up to Boston to see my great grandmother from time to time and to see family. I don’t really remember it though and we never really went out and did touristy things… not that I recall! So as I planned our trip up to Maine and saw that we would have to switch trains in Boston, I thought it would be fun to stick around for a little exploring. Mr. Actually had never been and didn’t know much about it (aside from having seen Good Will Hunting and The Departed) so we planned to spend 2 nights having a little wander though one of the oldest cities in America! We packed a lot in (including a trip to Salem!) so I’ve got a lot to share!

Being a New Yorker, there’s a natural rivalry with Boston (I made sure not to wear my ‘New York’ sweatshirt just to be safe) but I have to admit, I did enjoy my time there. Exploring a new place is always exciting… looking for places to eat, googling the sites and figuring out how we want to spend our time. It was a little strange to see places that I remember learning about in school, though I did have to whip out my phone to look stuff up because I couldn’t remember every detail.

Chinatown

Our first order of business when we got into Boston was to get something to eat. We wanted something low-key and I had discovered that the food in Chinatown was meant to be unrivalled. I had a few spots saved, like Dumpling Cafe (Chinese), Pho Pasteur (Vietnamese), and Taiwan Cafe (Taiwanese). Despite being called Chinatown, it’s more of a melting pot of cuisines so you’ll definitely have options! We ended up going to Dumpling Cafe and I can confirm that the dumplings were delicious! We took our leftovers back to our hotel and had them for dinner the next night too… those portion sizes were no joke!

Beacon Hill

Want to see some quaint and picturesque streets? Head to Beacon Hill. It’s one of Boston’s oldest neighborhoods and features some delightful cobbled streets. You’ll find Acorn Street in Beacon Hill, which feels like it’s right out of the 1800s. There were lots of people there taking photos (don’t blame them to be honest) but that’s something to bare in mind if you’re planning on walking around. We also stopped off at Beacon Hill Books because I just couldn’t resist. It’s a bookshop inside a townhouse and it’s an absolute dream. I could have stayed there for ages to be honest. There’s a little cafe in the basement too if you fancy, but we decided to get some hot spiced apple cider to take with us as we carried on walking!

Boston Public Garden

Right next to Beacon Hill is the Boston Public Garden. It’s a lovely little spot with lots of trees and and a lake. If you’ve seen Good Will Hunting, there’s a pivotal scene that take place on one of the benches here. We walked by it (though didn’t realise at the time) and took a stroll across the bridge and just enjoyed the general splendor. The trees were starting to turn a little bit and I can only imagine how lovely it would be with all those autumnal colours. Having a bit of green space is always something I appreciate (especially living in London) so it’s worth a visit. Once you’re done walking through the greenery, drop by Brattle Book Shop, one of America’s largest and oldest bookstores.

Regina Pizzeria

I found Regina Pizzeria when I was looking for a spot to grab lunch before we caught our train up to Portland. It came highly recommended and I’m going to tell you right now, it did not disappoint. Tucked away in the north end of Boston, this pizzeria offers brick oven pizza and a fun relaxed atmosphere. It really ticked all the boxes. Mr Actually commented that he loved how local and no frills it was, and he felt like he’d stepped into a movie set or something. Matt Damon is that you in the corner with Ben Affleck? Not quite but it definitely had that vibe. The police department patches all over the walls certainly helped. Still, the atmosphere was perfect and the pizza was delicious too, well worth the wait – there’s no booking, it’s just first come first serve and people line up outside and get called in. We loved it so much, we went back on another day!

Boston Public Library

In our final few hours in Boston, the weather took a turn for the worst and we were faced with torrential rain and nothing to do. So I did a little googling (literally, ‘what to do in Boston when it rains’) and boy did we end up finding a gem. The top suggestion was to head to the Boston Public Library. So we hopped on a bus and made our way over, seeking refuge from the rain. What we found was quite possibly the most beautiful library I’ve ever been in?

The Freedom Trail

Here’s the thing – Boston is one of the oldest cities in America, so naturally there are some pretty fascinating points of history you might want to visit. Independence Hall or Paul Revere’s house perhaps? You’re likely going to find a lot of them as you walk around Boston anyway (it’s a very walkable city but does have some public transport too!) but if you want to make sure you’re following the official Freedom Trail you can do that too. There are markers all over the city that will point you in the right direction. Making sure you hit a few of these spots and brushing up on your American history is a must if you’re visiting Boston!

There you have it – just some of what we got up to in Boston. It’s only a 4 hour train journey from Penn Station so if you’re heading Stateside, I’d definitely consider a trip! There’s so much more to do as well. The weather scarpered our plans just a bit so we didn’t even scratch the surface. Honestly, I’d go back for that pizza and another Boston Cream Pie and be one happy camper.