How to Spend a Long Weekend in Boston, Massachusetts

This March my sisters and I spent a long weekend in the East Coast town of Boston. Only a 4 hour train ride from New York City, it has something for everyone to enjoy! Come along as I share how we spent our time in the “Old Bay State.” Shoutout to my older sister, Amy, who did most of the planning for this trip and made it as fun as it was! She has a knack for finding the coolest places and things to do.

Day 1

We flew in on a Thursday afternoon and started to make the most of the day as soon as we touched down. After getting to our hotel, we took the subway to James Hook for some high anticipated seafood 😛. Here I learned that lobster is not my favorite. Although, I understand the hype surrounding lobster rolls. The crab cakes and lobster bisque were tastier to me.

With full bellies and happy taste buds, we walked to the Boston Public Library. Surrounded by marble and sky high ceiling arches, I felt like I was in the Library of Congress. The public library is a must-see in Boston!

While we were in this area of the city we walked down the picturesque Acorn and Newbury Streets. Make sure to also stop by Brattle Bookshop. This outdoor bookstore was unique and worth the stop although we didn’t purchase any literature. Finally, we explored China Town and enjoyed rounds of dim sum at Winsor Dim Sum before sunset.

Day 2

We started this day early in order to get coffee and make our way to Harvard. After exploring the iconic campus and people watching, we worked up an appetite. “What? Like it’s hard?!” To curb our appetite we dined on gyros, fries, and feta (oh my!) at Saloniki Greek in Cambridge. Make sure you stop by Mike’s Pastry (‘Home of the Cannoli’) to try one of their iconic cannoli for dessert.

Perhaps one of the most iconic things about Boston is its harbor where so much of U.S. history took place. Stepping aboard the U.S.S. Constitution and visiting the museum provided a glimpse into what life was like during the revolution. Fan Pier park also gives you great views of the city’s waters. Walk down the pathway for views of ships coming into harbor. If you’d prefer a bird’s eye view of the shore, head to the 14th floor of Independence Wharf Building. After checking in with the staff at the front desk you can ride the elevator to the top for no cost. Be sure to plan ahead as it closes at 5pm.

On our way back to the hotel we stopped at Citrus & Salt for dinner. This fresh and modern Mexican restaurant was delicious (and super busy!). I particularly enjoyed the goat cheese nachos.

Day 3

Tatte (like latte) Bakery & Cafe provided fuel for the third and final morning of travel. We got lucky and got a table but the line was often out the door. Caffeinated and ready to go, we made our way to the Isabella Stewart Gardner Museum. This museum is home to the largest art heist in history. We honestly didn’t spend as much time here as we thought but enjoyed walking through all 4 floors of art and checking out the gift shop . Half of the time was spent taking in the stunning courtyard entrance. The MassArt Art Museum is also nearby if you want more art.

When I woke up on Day 3, I didn’t know that I would be having the best pasta of my life a few hours later. But boy was I pleasantly surprised. Let’s just say history buffs aren’t the only ones who will enjoy the Boston. If you consider yourself any level of foodie, you’ll be sure to enjoy yourself. By far the best meal we had was in Little Italy at Carmelina’s. To this day my sisters and I talk about the mushroom rigatoni we had. If I ever find myself back in Boston, I would make it a point to stop back at this restaurant. Be sure to set a reservation as this is a popular place.

Quincy Market and Boston Public Market were the last stops on our journey in the city. We wandered through an outdoor market overflowing with fresh produce. Inside, vendors were selling all sorts of products, foods, and drinks.

Where We Stayed

The Revolution Hotel was a subway ride away from most of our destinations. It was clean, comfortable, and modern. Although separate bathrooms were down the hall, it ended up being just what we needed after exploring the city all day.

How We Got Around

My travel companions and I Ubered to and from the airport and hotel. Once you get to the main city, most things are accessible by foot or public transportation. A weekend pass only puts you out $8 and is far cheaper than ordering Ubers.

What I Would Have Done Differently

The weather was rainy and chilly during the end of March. Looking back I wish I would have brought more layers and a hat. Because of the inclement weather we ended up trying to find mostly indoor activities. If I ever go back to Boston on a sunny day I would be sure to check out more outdoor historic sites. Some of these include the Paul Revere House, Boston Massacre Site, and Great Molasses Flood. Also, Harvard offers walking tours of their campus. I would have loved to see more of the campus and learn about its history. You live and you learn! I hope this gave you some great ideas of how to spend your long weekend in Boston!

Coming Soon (more Portugal content 🙂): Everything I Did in Porto, Portugal