3 Day Boston Itinerary + A Review of our Trip
A view of downtown Boston from Boston Common.
For a while, I didn’t think of Boston as an American city where everyone should visit (as opposed to places like L.A., New York City, Miami, or Chicago). But after visiting Boston for the second time in a year, I was proven wrong. This city is filled with history, culture, public spaces, renowned sports teams, and — this came as a surprise for me - delicious food. This blog recounts what my family and I did during our weekend trip to Boston. We went for my graduation from grad school so those respective activities took up some of our time. At the bottom of this post, I’ll include recommendations for things in Boston that I’ve done before as well as things that I wish I had the time to do (which means I’ll have to return for a future trip!). Read on to start planning your trip!
Day 1
Itinerary
Land in Boston and check into Airbnb (here’s the listing — the Airbnb was great, but it wasn’t as accessible by public transit as I thought it was going to be)
Head to North End. Walk along the main street (Hanover St.) and explore the area.
Dinner at an Italian restaurant in the North End (we dined at Trattoria Il Panino)
Celtics game at TD Garden (we got our last-minute tickets on the Gametime app)
Overview
We didn’t land in Boston until late afternoon, so the first thing we did was take an Uber from the airport to the Airbnb, which was located in the town of Sommerville. The airbnb is just a 15 minute car ride to downtown Boston. I realized that Boston is unlike cities like Atlanta and Houston. Boston itself isn’t that big and the surrounding areas are technically their own cities with their own municipalities. Still, I considered all of this to be “Boston";” as a non-Bostonian, don’t get mad at me about this!
Once we got settled in the Airbnb, it was already around dinner time. I was getting hungry and didn’t get the chance to explore the North End neighborhood the last time I was in Boston. I recommended to my family that we should get a nice Italian dinner a at a restaurant there. A friend who’s from Boston told me that making an advance reservation wouldn’t be necessary; there’s so many restaurants in the area that at least one should be able to seat us). It was a Friday night smack dab in the middle of dinnertime, so most of the restaurants were packed. After walking and looking around for about 10 minutes, my dad found a restaurant with an available outdoor table. It was perfect. The restaurant was Trattoria Il Panino, and honestly, we couldn’t have found a better place. The service was prompt and the food was hot and delicious. We ordered fried calamari and the assorted vegetable antipasto for the table. I ordered the pesto pasta (chef’s kiss), Abraham had the lobster ravioli, my mom had shrimp scampi (she was disappointed that it was served with spaghetti instead of linguine), and my dad ordered plain spaghetti and meatballs (which has been the only dish he has eaten at Italian restaurants since I can remember).
While I was wolfing down my food, my dad suggested that we go to the Celtics vs. Heat playoff game that was taking place that night. I instantly pushed the thought out of my head because, well, a few reasons: 1) I prefer planning to spontaneity and 2) I didn’t think tickets were even going to be available 30 minutes before the game started. But my dad mentioned how it would be a special experience since it was a playoff for who would advance to the NBA Finals and soon my mom and Abraham were agreeing. Abraham was able to find 4 seats together (miraculous) and we secured them as quickly as we could. Once I received the confirmation email, I started feeling excited; the street was packed with fans in their Celtic green. The energy in the air was electric and palpable. For once, I was happy to go with the flow.
We had a great time at the game. The arena was packed and I personally found more entertainment from the fans seated around us than the game itself. It was Abraham’s first NBA game and I’m happy he was able to get that experience. Unfortunately, the Celtics lost. If they won, it would’ve been a party spilling it on the streets. Regardless, it was an incredible experience that I’ll keep with me for a while.
Day 2
Itinerary
Attend Harvard Graduate School of Education’s (HGSE) Commencement in the morning
Eat and socialize at the HGSE Block Party
Catch the Champion’s League Final game (Real Madrid vs. Liverpool) at a European-style Pub (we ended up at The Banshee)
Dinner at Empire Boston (one of my favorite restaurants ever. It also turns into a club after 9 pm)
Flex Time
Overview
Half of the day was spent doing graduation things. I was able to hear my name called and walk across the stage. It was a beautiful way to celebrate my “Harvard moment” with the three people I love the most: my mama, daddy, and husband. After the ceremony ended, my school organized a block party outside of the administrative buildings. I was able to see classmates in person that I only saw virtually, reconnect with old friends, and eat party-style food like pizza, pretzels, and mac-n-cheese (I truly love all three of these things).
After we were wrapping up at the block party, Abraham wanted to catch soccer teams Real Madrid and Liverpool play each other in the Champions League Final. Since Boston is a part of New England, he thought it would be a good idea to watch it at a European-style pub because the atmosphere would be full of excitement. My mom — who is a Liverpool fan — agreed. Even though I was exhausted from such an early morning, I was down. Abraham researched the best place to watch European football (aka soccer) in Boston and an Irish pub called The Banshee was recommended by numerous different people. We took an Uber to the pub, which was located in the Boston neighborhood of Dorchester. Dorchester — once its own city — is now Boston’s largest and most diverse neighborhood. Historically and presently, Dorchester has been a community where people from different parts of the world now call home.
The Banshee ended up being the closest we could have gotten to an authentic fútbol match. The bar was actually filled with a lot of people from Europe (specifically Irish people) and the amount of chanting, yelling, and profanity made it one of the most exciting and new experiences I’ve had in a while. Abraham was supporting Real Madrid, so naturally I also supported them. Real Madrid ended up winning! Afterwards, I made reservations for a hip Asian restaurant called Empire Boston. Abraham and I went there when we visited Boston last year and it was some of the yummiest food I’ve ever had. I highly recommend it! The night was still young after dinner, but we were so exhausted that we ended up going back to the Airbnb and having an early night. Besides, we had to get up around 5 am the next day to prepare for the next day’s festivities.
Day 3
Itinerary
Attend the Harvard All-University Commencement
Take photos and walk around campus
Brunch at Buttermilk + Bourbon
Rest break at the Airbnb
Head to downtown Boston and visit the Boston Common and gardens
Stroll around Beacon Hill (Pro tip: do the FREE self-guided virtual Black Heritage tour)
Grab dessert at Modern Pastry back in the North End
Overview
Graduates had to report to our meeting place by 6:25 in the morning. The entire family got up early to uber to campus together, so tuning in to bed early last night was the right choice. The University-wide Commencement was seeped in traditions dating back to the conception of Harvard as an institution (so it was complete with silk-rimmed top hats, canes, and a very theatrical Sheriff). After commencement, we took some photos and headed to our brunch reservations.
I chose New Orleans-stye Buttermilk + Bourbon as our brunch spot. Their menu looked really good online but the overall experience there was just a bit underwhelming (the fluffy biscuits, though, were to die for). After brunch, we went back to the Airbnb for a much-needed nap/rest break (we got up at 5 am). The weather was perfect that day, so after the nap we went to Boston Common to walk around and enjoy the greenery and sunshine. After spending some time at the park, we walked a few block over to the historical Beacon Hill neighborhood. Last year, Abraham and I walked around this neighborhood for the virtual Black Heritage Tour and I knew I wanted to return and take photos. My mom enjoyed the old Europe feel of the cobblestone streets and historical homes. As a history buff myself, I appreciated the different placards that identified homes where notable figures in history lived.
Afterwards, we walked about 20 minutes through the city to get to the North End. During the walk, we passed a cool outdoor park with large swinging chairs and a fountain (after consulting Google Maps, I learned that it’s the Rose Kennedy Greenway). I wanted to go to the North End to stop by Modern Pastry to get red velvet cupcakes. Abraham and my mom were hungry, so we stopped to get some pizza first. Afterwards, we stood in line at Modern Pastry and almost got to the front, only to learn that they’re cash only! I learned that Mike’s Pastry, the other super-popular Italian dessert shop, is also cash-only. Luckily, there was an ATM. across the street. We took out cash and got back in line, but luckily, it moves quickly. Modern Pastry didn’t have any red velvet cupcakes left and I was devastated (they truly have the BEST red velvet I’ve ever had in my life). But my mom was able to enjoy a few different European style desserts (which she loves…I’m more of an American-style, cake and icing kind of gal).
After we left Modern Pastry, we ubered back to the Airbnb and got ready to hit the hay. My family had an early flight that they had to catch. My flight wasn’t until later in the afternoon, but I spent the next morning sleeping in until it was time to check-out of the Airbnb. The weekend’s festivities left me feeling utterly exhausted.
Other Boston Recommendations
Isabella Stewart Gardner Museum (or any museum in Boston — it’s a museum city!)
Boston Public Garden
Red Sox Game at Fenway Park
Cruise or Kayak on the Charles River
Walking along a Charles River promenade
Rooftop bars such as Over the Charles Rooftop or Lookout Rooftop and Bar
Thanks for reading! Have you been to Boston before or plan to visit? If so, let me know your thoughts in the comments below!
