3 Days in Boston, Massachusetts

My boyfriend, Kevin, and I recently got back from our 3 day weekend trip to Boston, Massachusetts over our university fall break. Even though the weather did not start out great to say the least (there was a nor’easter!), it ended up being a really good weekend of exploring, learning, and fun for the both of us. We didn’t get to absolutely everything on my pre-planned itinerary that I had made weeks in advance, but I am happy with what we were able to do in our short amount of time! Everything that we didn’t get the chance to do is just going on my list for next time I visit.

Day One

Our first day began on Friday morning at 5 am when we woke up to leave for the Philly airport, where we took a an 8:45 am flight to Boston Logan. Since our flights there and back were so early, we opted to drive my car to the airport and parked at Colonial Parking (south of the airport) and paid only $30 for the whole weekend.

Once we landed in Boston after the long and grueling 45 minute flight, we were able to be in a Lyft (use code: MAYS70355 for $$$ off your next ride) and at our hotel by 11 am! We stayed at the Courtyard Marriott Boston Downtown because it was a great location (near just about everything) and it was relatively inexpensive compared to the other hotel and AirBnb options around the city. Our room was also available for check-in as soon as we got there without paying any early check-in fees, which was awesome! If it hadn’t been ready, we would have just left our bags with the front desk so that we could begin exploring the city.

The first thing on our itinerary was to walk some of the Freedom Trail. When we got there the rain and wind were not too bad, so we walked through the Boston Common to the start of the trail. We followed it to the Massachusetts State House, which we found out gives free 45 minute tours every hour (a happy accident). The tour was honestly really interesting and I definitely recommend doing it if you have not yet (my friend from Boston said she’s never even done it). Our guide was the sweetest old woman who knew just about everything about Boston and the surrounding area. She took us through each room in the building and told us the extensive history behind each painting, architectural feature, and statue. We even got to go into the voting rooms of the House of Representatives and the Senate (the history nerd inside of me was screaming).

After our tour was over, we ventured back outside where a tropical storm was raging on. We decided to brave the weather and continue walking the trail, skipping over and just walking by some places (including the site of the Boston Massacre) to get to Fanueuil Hall and Quincy Market for lunch. I honestly, for the life of me, cannot remember where exactly we got our lunch from. I just know that it was one of the overpriced lobster roll restaurants and it was absolutely delicious.

After lunch, we headed to the North End to see the Paul Revere house. It was $4.50 each with a student ID or $5 without, and we basically just took a self-guided tour through the tiny house that Paul Revere and his family once lived in. It was definitely cool to see, but it’s not something I would put at the top of your priority list (unless you’re a real Paul Revere enthusiast). Then, we walked over to the Paul Revere monument and walked around the area until it started torrential downpouring and we decided that we could no longer continue to brave the weather. So we called a Lyft and headed back to the hotel to relax for a little while before dinner (we were up since 5 am).

Later that night we went to dinner at Lolita’s in the Back Bay, which was SO COOL. You have to go the next time you’re in Boston because it was just a really fun experience (the food was very good, but go for the ambiance). Make sure you make a reservation because it gets crowded on the weekends. When we first sat down, our waitress brought out a palette cleanser which was a smoking bowl full of a grapefruit shaved ice with tequila poured over it. Then, Kevin ordered a Corona michelada style, which was with salt, lime worcestershire, and house made hot sauce, and I got a strawberry basil mojito. For dinner I got chicken habanero tacos, Kevin got the steak sofrito quesadilla, and we shared the corn empanada appetizer. Arguably the best part of the whole meal was when the waitress brought out a giant watermelon cotton candy covered in Pop Rocks with our check. It was huge and I don’t even usually like cotton candy, but you can bet that I ate the entire thing (with a little help from Kevin). After our meal, we went to Solas, an Irish pub at the Lenox Hotel, for post-dinner drinks with my G-Big because she lives right outside of Boston and I hadn’t seen her in over 2 years!

Day Two

We began our second day with a bit of a late start since we were so tired from being up so early the day before. At around 10 am we walked over to the Tatte in Beacon Hill for sustenance and were met by a lot of people with the exact same idea. Tatte was very crowded, but my faith in humanity was restored when a kind woman came over to me when she was finished eating and offered Kevin and I her table since she overheard us talking about eating outside in the rain. I got the apple monkey bread pastry and the house oat milk latte, which was probably one of my favorite coffees I think ever. Kevin got a bacon, egg, and cheese sandwich plus a black coffee, and we also got an almond croissant to share later in the day. I would literally kill for a Tatte to open up anywhere near me. Not only was the food and coffee amazing, but the aesthetic of it was just so dang cute and comforting. I’d love to sit there and do homework or chat with a friend.

After I obsessed over Tatte for a while (and the fire alarm actually went off, so we had to go), we walked over to Acorn Street and took the typical touristy pictures. Beacon Hill was picturesque and serene even in the rain.

We decided to then take a walk through the Public Garden to take some pictures and see all the various statues throughout the garden.

That afternoon we headed down Newbury Street for some window shopping and made our way to the Public Library. I underestimated just how pretty the inside of this building would be! It was very similar to the New York Public Library if you’ve ever been there. Next time I’m in Boston, I want to also have afternoon tea at the fancy tea room inside the library.

Afterwards, we began the long walk all the way to Fenway Park, where there was, unfortunately, no game going on because the Red Sox are already out of the playoffs. If you have never been and it is baseball season, I definitely recommend going to a game at Fenway because it is an experience like no other! When I was in Boston a couple of years ago, I was able to go with my friends for only $9 each for standing tickets. As long as you’re able to stand for the entirety of the game, these tickets are perfect because you have a great view and are truly in the center of the action the entire time. I was really hoping that the Red Sox were going to make it to the playoffs so Kevin and I could see a game. Regardless though, we walked around the outside of the stadium and explored the area a bit. We opted not to do the stadium tour just because we did not feel like we needed to. Instead, we got lunch at Lansdowne Pub right next to the stadium. I ate a turkey sandwich and Kevin ate a plate of sausage, hot pretzel bites, various dips, and pickled veggies. Sitting in this pub truly felt like I was sitting in Ireland with the Gaelic words all over the walls and the almost-gothic furniture and decor. It was the real deal and delicious too.

We decided to make the long, almost 40 minute, walk back to our hotel so that we could relax a bit before dinner and the rest of the night. That night we were planning on getting Italian food in the North End, which is Boston’s Little Italy. If you listen to any one piece of advice from this blog post, make it be this one: make a reservation SOMEWHERE in the North End, especially if it’s a Friday or Saturday night. I didn’t know this, mainly because I went into the night with the intention of eating at Giacomo’s, which doesn’t take reservations, but also almost always at least an hour wait out the door. If I could go back, I would make reservations at either Carmelina’s or Bricco, my second and third choice of restaurants, both of which took reservations. We ended up eating at Forcella, which was absolutely delicious and I definitely recommend, but it was pretty expensive even compared to the others. For dinner, I got the Rigatoni alla Sorrentina with a glass of red wine, and Kevin got the Linguine al Pesto and a beer (typical). Both were yummy.

After dinner, we walked over to the waterfront for a Ghosts & Graveyards tour to all of the haunted spooky sites around the city! Kevin and I both expected it to be much scarier than it actually was (he was so relieved). It was mainly just scary stories from history told by a ghost walking around various graveyards throughout Boston. Definitely worth the money, but just not totally what we were expecting.

Day Three

Our last day in Boston just happened to be the same as free ferry day in the Boston Harbor, so we took full advantage and went early to get tickets! I was worried that it would be sold out, but we got to the harbor around 9:30 and got tickets for the 11 o’clock boat. We then had time to walk over to a Persian breakfast place called Kolbeh right across from the harbor. All I have to say is huge portion sizes, relatively cheap prices, and incredible food. I had a Mediterranean omelet with potatoes and toast, and Kevin had the steak kabob and eggs with potatoes and toast.

After breakfast, we boarded the ferry honestly thinking that it would be a 45 min to an hour ride total. About 30 minutes into the ride we realized that it was 50 minutes to St. Georges Island, where we would stay about an hour, and then 50 minutes back. Needless to say, check where you’re actually going and how long you’ll be gone before you get on a boat. Anyway, the ferry ride was really quite relaxing. The weather also got so nice on Sunday and the sun felt amazing. At St. Georges Island there was an old military fort/POW camp that we toured, which actually ended up being really cool.

When we got back later that afternoon, we walked next door to the New England aquarium also right in the harbor. Kevin loves aquariums so we spent an hour or so looking at fish, giant sea turtles, and my personal favorite, sea lions (sea lions have been one of my favorite animals after seeing them at La Jolla in California a few years ago). Honestly, I think the aquarium was worth it just because of the sea lions.

Once we decided we’d had enough of the aquatic animals, we walked down the Harbor-walk and through the Seaport all the way to Harpoon Brewery. We planned on doing a tour, but after walking literally 40 minutes there, they told us that they stopped doing tours for the day (even though it was only 4 pm and they said they stop at 5 on Sundays???). After getting a little upset and a little bitter about that, we realized that we were starving because we had not eaten since breakfast, and set out to find some food asap. We argued about restaurants for a little (because that’s what we do), but finally decided on the Barking Crab and boy, am I glad we did. This place was so much fun, so delicious, and just a great experience! They only had outdoor covered seating in this big tent since it was so warm out and seating was very limited. When we got there, the hostess said 45 minutes, but I swear I got the text that our table was ready in less than 10! It was perfect because we were so hungry. We first started off our meal with some drinks (beer for Kevin, Truly for me) and a fried calamari appetizer, and it definitely did not disappoint. Then for dinner, I got the fish and chips, and Kevin got the snow crab legs. The restaurant itself was set up totally outdoors, like I said, and everyone sat at picnic tables together. Although the atmosphere was very laid-back and casual, the food was amazing and the prices were definitely not laid-back and casual. Honestly though, it was worth it (and Kevin really loved his crab legs).

We finished off the night at the Ben & Jerry’s across the street: Kevin got a waffle cone with Americone Dream and I got a cup with Americone Dream and Chocolate Fudge Brownie (no pictures, just memories).

Overall, I had such a wonderful time this weekend in Boston. It is such a cool city with an eclectic vibe and really a lot to do. I will definitely be back, hopefully soon!

3 Days In Boston