I’m back with another look back at one of our trips! For our one year anniversary, we did a long weekend in Boston. This was really our first time walking into a city that we only knew a little about without much of an itinerary, and just seeing where local recommendations took us!
Boston is the perfect spot for a long weekend. With its public transportation infrastructure, the city is super easy to get around, making it ideal for exploring the major sights, as well as finding some hidden gems!
I had been to Boston and Cambridge a couple times, so I had a really basic understanding of where things were, but mostly just knew how easy it was to get around. So when looking for a place to stay, we prioritized two things: cost and proximity to public transit. After a good bit of searching, I found a home in Roslindale (southwest of the city) that functioned kind of like a hostel - you had a private room, and shared a hallway bathroom with one other room. We shared our bathroom with a couple from Australia that were full time nurses in Indigenous tribes that didn’t have easy access to healthcare. Needless to say, we enjoyed our conversations with them over breakfast, listening to stories and enjoying the experience that traveling in shared spaces offers!
But, the best parts for us: they offered breakfast and...they gave you an unlimited transit pass to use during your stay! Literally, like an $80/person value on a room that cost $250 total including all fees for 3 nights. We were a 5 minute walk from the train station, which took about 30 minutes to get downtown. Unfortunately, I couldn’t find the listing anymore, but this is an amenity I always keep an eye out for!
So here we are, feeling like the city is at our fingertips, armed with the ability to hop on and off all busses, trains, and trolleys, and only two things on the agenda: a baseball game at Fenway Park, and a late night improv show at Improv Asylum (two things we’d highly recommend doing).
Our train (called the T in Boston) went right past the original Sam Adams Brewery, so obviously we hopped off for their free tour, which also comes with free beer! We were there in May, and they were still serving their 26.2 brew, which is made specially for the Boston Marathon, and only served in the city. It was so good, and something we sought out at places the rest of our trip!
Then, we hit the T towards downtown, and got off at Haymarket. The station is right underneath Boston Public Market, and let me tell y’all if you don’t know already. We love public markets. They are one of the top things we search for in going to a new city, and rarely does one disappoint. We walked inside to this explosion of local goods; beautiful wood pieces, locally sourced yarn, hand-crafted jewelry, and some incredible food. Fortunately for our wallet we avoided souvenirs, but instead decided to sit down at a local brewery’s booth, called Hopsters. Their beer glasses still sit on our kitchen shelf! Afterwards, we grabbed some food from Red’s Best Fish Market, which is a permanent staple in the market.10/10, highly recommend.
As if we hadn’t had enough market time, we took a quick walk over to Faneuil Hall Marketplace, which is a beautiful, iconic building that’s home to a ton of shops and food, and is right in the middle of so many historic places!
After all our time on planes and trains, we were ready for a good walk. Granted, we’re always up for pushing the envelope on how far is acceptable to walk in a new city. But, the Boston Tea Party site was only about a mile away, which is quite tame in our book. On the way, we hit the Boston Massacre Site and Old South Meeting House. We decided not to pay for the Tea Party Site tour, but were still able to see basically everything at the location anyways. If memory serves me right, you can’t get on the ship without the tour, but that’s it.
By now, it was time to head to Fenway, so we found a train station, and got to the game as soon as the gates opened to walk around and explore the stadium. As a big time baseball fan, it was an amazing place to explore, and definitely a highlight of the trip!
The next day, we were already pretty tired, so we took it easy in the morning before grabbing a train to Chinatown. Boston has a beautiful Chinatown Gate, and obviously so much great food in the neighborhood.
But, our major destination for the day was Cambridge, so we moved through Chinatown pretty quickly before taking the train to Harvard Yard. The area around Harvard is just so beautiful, and was so fun to slowly explore. There’s a ton of great coffee shops and bookstores to get lost in, and even if it seems out of the way, the T makes the trip so quick. Even on a short trip, wandering around Cambridge is a great choice!
We made our way back downtown to visit Improv Asylum. I had been before on a high school trip, and the team there does such a fantastic job. There’s a ton of great entertainment in Boston, but this crew is so fun to watch. It’s underground, and the stage is surrounded by seats on all sides. Each show is different, and their team are all pros. If you find yourself in the city at night looking for something to do, this show doesn’t disappoint!
Well, I think that’s it. We loved our time here, and feel like we played our cards pretty well. If we were to go again, I’d definitely be on the hunt for an Airbnb with a transportation pass amenity, or be willing to spend the extra money to stay centrally located. Regardless, you’re probably still going to run up a T tab, so for us, it’s worth the extra searching! In just a weekend, we didn’t try to get up to Cape Cod at all, but with one more day, that would’ve been top of our list to hit next!
