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A Long Weekend in Boston

Since I moved back to PA from Boston at the end of August, I can't help but miss all of my favorite spots in the city where I spent my first post-grad year. These last few weeks since my move have been busy with unpacking, starting a new job, and spending some much-needed quality time with family and friends. I am so excited to finally share this guide, which has been a year in the making and a long time coming. Please enjoy my recommendations for food, drink, and things to do in Beantown!


Since I have far more to share than a long weekend's worth of activities and restaurants, I'm framing this guide as a four day trip with my most favorite spots highlighted, as well as some honorable mentions. Of course, not everything on my lists can be checked off in one weekend, but there's always opportunities for return trips to Boston in the future.


Having lived in the South End for a year, I'm biased to this neighborhood, but truly is is a great area!


Day One: Thursday


Start your long weekend in Boston with a stroll down Commonwealth Ave. and into the Boston Public Garden & Commons, where you'll be rewarded with views of the city, green spaces, and a bit of tranquility in a bustling city. Grab some breakfast and coffee from one of Tatte's many locations throughout the city, watch the swan boat riders, or rent your own.


When the weather is nice in Boston, the Public Garden is a great outdoor spot


After the Commons, head over to Beacon Hill to wander through the cobblestone streets and beautiful brownstones that make up one of Boston's most picturesque neighborhoods. Some of my favorite boutiques and gift shops are on Charles Street. While I know this restaurant is only open for lunch on the weekends, I recommend Toscano as a fabulous spot for great pasta and even better wine in this part of town.


Newbury Street, Boston's famous shopping avenue, is a must for a weekend trip to the city. After you shop 'til you drop on both Newbury and in the Prudential Center, the indoor mall on Boylston adjacent to the finish line of the Boston Marathon, check out Eataly (inside the Pru) for an indoor Italian market and your choice of restaurants.


An Italian brunch: start with Terra's ricotta and cocktails


I've been to Eataly's Terra, pictured above, for both brunch and dinner. It's safe to say you cannot go wrong with the food here or at La Pizza & La Pasta, both situated within and above the Eataly market in the Pru. Terra has a garden-like atmosphere with an outdoor, rooftop patio, so it can also serve as a great spot for drinks in the evening as well.


To walk off that Italian food and dive into Boston's history, spend the afternoon exploring the Freedom Trail, a 2.5 mile walking tour that takes you through various sites from the American Revolution. Tours are always offered if you're interested in truly learning about the spots, but plenty of visitors take the self-guided route as well.


I had only heard good things about Mariel, a Cuban restaurant just outside Downtown Crossing with quite the photogenic interior, throughout my time in the city. I finally got a reservation here a few weeks before I moved out and I'm so happy I was able to try it. Mariel boasts an extensive drink menu of mojitos, cocktails, and wines to pair with small plates or "street" pizzas. Check out this spot for dinner, but make a reservation far in advance as it is pretty popular!


Honorable mentions for restaurants around Back Bay & Downtown Crossing: Buttermilk & Bourbon (a taste of New Orleans), Citrus & Salt (Mexican), and Dillon's (American).


Day Two: Friday


Let's spend a day in Boston's South End! Since I lived in this neighborhood in an apartment off Washington Street, I tried my fair share of local spots. Start the day off with coffee and breakfast sandwiches at Farmer's Horse, or brunch at South End Buttery. Shawmut Avenue in South End is one of my favorite streets, and my old yoga studio along with some cute shops are also along this street.


Like I said, I may be biased, but South End is stunning. Like Beacon Hill, gorgeous Victorian brownstones make up most of this neighborhood and offer a peaceful area to walk around. If you're here on the weekends, check out the SoWa Market for art, fresh produce, and other local finds. Since it has been under construction the last year, I was never able to tour the Christian Science Center, halfway between South End and Back Bay, but I did visit the Mary Baker Eddy Library's Mapparium. If you've never heard of a mapparium, you're not alone, but don't discredit this museum. Patrons are able to walk through a three-story stain-glass globe where a whisper can be heard from anywhere in the room due to the acoustics.


Head back to Shawmut Ave. for lunch at Kava Neo-Taverna for Greek small plates and quaint outdoor & indoor seating options. This place is always popping with both locals and tourists; reservations open at 7am for same-day requests on Resy.


Tip: check out the MFA's special exhibitions that run for limited times


A quick ride on South End's green line westbound to Heath Street brings you to Boston's Museum of Fine Arts, which boasts beautiful collections including French impressionist and post-impressionist paintings, Ancient Egyptian artifacts, 18th- and 19th-century American art, and more. I spent an afternoon at the MFA during my last week of Boston, but truly wish I had come more often so that I could dedicate hours to each exhibit. The Monet gallery is my personal favorite, as well as the collection of Van Goghs.


A South End gem: Toro


To finish the day in South End, head to Toro for one of the best spots for tapas in town. The restaurant is small, so book your reservation in advance, but they recently opened a backyard patio for outdoor seating. I've been here several times and truly enjoyed each meal. Favorite tapas: pan con tomate, patatas bravas, maíz asado, burrata, and empanadas, but everything is fabulous.


Honorable mentions for South End restaurants (since I could go on for days): Banyan Bar (Asian fusion), Beehive (marketed as Bohemian, has a great bar and live music), El Centro (Mexican), and 3 Italian favorites - Mida, Coppa, and SRV. Delish!


Day Three: Saturday


A trip to Boston would be incomplete without seeing the beauty of the Boston Public Library. The McKim Courtyard is a picturesque, open-air space that holds concerts and other events throughout the year, adjacent to Courtyard Tea Room is a great spot for brunch with a fixed menu and tea with views looking into the Courtyard. When my mom and I had tea here, we watched a cello concert and were in awe at how lovely the brunch & tea were served.


BPL's McKim Courtyard


Copley Square, directly outside the Boston Public Library, holds an open market from 11am - 5pm, May - November. With over 70 vendors, this is another great spot to shop fresh produce, crafts and jewelry, and more. In the summer, I went here for birthday gifts, art for my apartment, and local fruits & veggies that were in season.


Before the evening's activities, have dinner at Lolita in Seaport for Mexican fare and tasty margaritas. I've always loved the vibe of this restaurant and brought my family here around New Year's to celebrate being together in the city. There are great restaurants in Seaport, but this is definitely one of my favorites in Boston overall. Honorable mentions in Seaport to follow!


If you're lucky enough to be in Beantown for a Red Sox game, a visit to Fenway is a must! Although I'm from outside of Philadelphia and will always root for the Phillies, Boston sports are so much fun, and I'll always be a Red Sox fan.


Reppin' New Balance in its home city!


Fenway is a great part in town with some of my favorite bars in the city, including Loretta's and Cheeky Monkey. These spots are always bustling on game day, but they never fail to provide a fun time.


Honorable mentions for Fenway restaurants: Blue Ribbon Sushi (one word: yum), Sweet Cheeks Q (Texas-style BBQ), and Time Out Market (an indoor food hall with various options for dinner as well cocktail bars and dessert spots).


Honorable mentions for Seaport restaurants: Coquette (French, owned by the same company as Mariel), Serafina (Italian), Committee (Greek), and The Barking Crab (seafood).


Day Four: Sunday


Enjoy your final day of the weekend with a stroll around Cambridge and Harvard Yard. This part of town has cute shops and yummy restaurants, so grab a bite for breakfast or some coffee while you're here. I've always loved taking a quick trip across the river for a change of scenery. The grounds of Harvard are beautiful, so you truly can't go wrong!


If you have extra time, pair your Cambridge tour with lunch at The Maharaja (Indian cuisine)


Finally, have lunch in Boston's famous Italian North End before hitting the road or heading to the airport. With so many restaurants within one little neighborhood, you're bound to find incredible, authentic food. Some of my favorite spots include Bricco, Parla, Giacomo's, and Trattoria Il Panino.


Boston is a great city to visit, and an even better city to live in. I have so many recommendations for various parts of the city, so always feel free to send me an email via my contact form on this site, or a DM on Instagram if you have any questions or requests beyond this guide!

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