How to Spend 3 Days in Boston

Boston is one of the most illustrious cities in the world, and for good reason. The bustling boroughs are rich in history, culture, and architecture, and the city is home to one of the most recognizable sports franchises in the world, the Boston Red Sox.

Boston had been on my bucket list for some time, but it wasn’t until I started exploring the neighborhoods that I realized how special the (self-proclaimed) city of champions really was. By day two, I was already picking out brownstones to move into.

Read on for how to spend 3 days in Boston, based on our travels and some amazing local recommendations!

Day 1 of 3 Days in Boston

Breakfast at Flour Bakery + Duck Tour

Eat breakfast at Flour Bakery on Washington Street and order the famous sticky buns and egg sandwiches before hopping on a duck tour by the Prudential Centre.

I know what you’re thinking, a duck tour?? Really? That’s what we thought too before it was recommended to us by multiple locals. It may seem cheesy, but it is the perfect way to get to know the city you will be exploring over the next few days and brush up on your Boston history. It’s only 90 minutes, so it’s a quick overview to help you get the lay of the land for your 3 days in Boston.

Boston Public Library

When you depart the duck tour, take a short walk to the Boston Public Library. This place ain’t your average public library, let me tell ya. You could spend all afternoon marveling at the detailed finishings, high ceilings and towering bookshelves. They just completed a very impressive $78 million dollar renovation on the McKim building. It’s interesting to walk through such a modern design before you arrive at the Johnson Building (home of Bates Hall, famous for the green lights lining each table). If I lived in Boston, I’d spend way too much time here.

Dig Inn for Lunch

Wander over to Dig Inn for a healthy lunch. This quick lunch spot gets BUSY, but their assembly line is something of an art. They focus on organic, healthy ingredients, and you can customize your bowl as you’d like. I opted for lemon quinoa with salmon, sautéed kale and sweet potatoes with vinaigrette and sriracha sauce. SO good. Really balances out the red wine and dirty vodka martini’s come happy hour.

Copley Square

You can explore Copley Square a little bit since you’re there. Check out the contrast between the tallest building in New England and the church to its left. This is a popular outdoor lunch spot for locals that work nearby.

Shopping on Newbury Street

Now that you have refueled, wander over to Newbury Street for an afternoon of shopping. I loved exploring this area, and was pleasantly surprised at how many local shops lined the street versus your typical big box stores. Here’s a list of my favorite local shops on Newbury street!

Wine Break at Saltie Girl

Ready for wine? We loved Saltie Girl, a cute seafood restaurant tucked away on Dartmouth Street. We had white wine, rose, and a delicious bowl of chowder while sitting at the beautifully decorated bar top. The bartenders are great for recommendations and happy to help answer questions!

Dinner at Bar Mezzana

This restaurant came as a recommendation from a few bartenders at Saltie Girl. It’s in the South End, so a great opportunity to check out a new neighborhood and eat some AMAZING Italian food while sipping delicious cocktails. Order the tasting menu to experience a highlight reel of the chef’s favorite dishes.

Special shout out to Gwen for writing out an entire list of local recommendations by neighborhood for us! 

Live Music at The Beehive

Walk over to The Beehive for live music and an after dinner drink. The drinks weren’t anything to write home about, but the atmosphere and live band were incredible. You can look on the website to see who is playing for the week. Ask some locals if they recommend a certain artist, as there are some brilliant performers in rotation.

Nightcap at Barcelona

This was one of my favorite restaurant/bars we went to in Boston. It’s a short walk from Beehive, and their wine list in B-A-N-A-N-A-S. Mark, the bartender, reminded me of a mad scientist, just sub out the beakers for wine glasses. He was so passionate and gave us a crash course on sherry, something I had never tried. I’ve always fancied a glass of port after dinner, but he gave us a detailed lesson and tasting on all the varietals sherry has to offer.

I was impressed. And drunk.

Day 2 of 3 Days in Boston

Quincy Market and Faneuil Hall

Have a light breakfast before heading to Quincy Market and Faneuil Hall. You’ll want to save your appetite for the abundance of food choices at Quincy Market. Boston Chowda Co is a fan favorite. For a great sit down place, try Zuma Tex Mex Grill.

Once you are done exploring the market and Hall, start walking the Freedom Trail towards the North End (Little Italy). Stop at the famous Union Oyster House, known for serving up chowder since 1826!

Mike’s Pastry

This place is notorious on the streets of Boston for their cannoli. We turned the corner and couldn’t believe how many people were there. It was packed, but don’t let the line deter you, it moves fast.

There is a debate as to which establishment holds the title for best pastries, Mike’s Pastry or Modern Pastry. I’ll let you try for yourself. Let me know which one you like better!

Trattoria Il Panino

Walk off the calories (totally worth it) and explore historic Little Italy. It was interesting chatting with locals as they said the Italian food in this area is a little overrated and commercialized. However, one place they told us not to miss was Bricco and/or Trattoria Il Panino (same owners.. all the restaurants by Depasqual Ventures won’t disappoint). The espresso martinis are heavenly and a nice afternoon pick me up.

Harvard

After taking a breather back at your hotel, uber to Harvard Square and explore the campus at golden hour. Grab a map of the campus and make sure you check out Harvard business school and Harvard Law (what, like it’s hard?)

When you’re done, explore the neighborhood near Harvard Square and have a glass of wine. From there, uber to one of my favorite restaurants in Boston, Sarma.

Dinner at Sarma

Sarma is a modern Mediterranean restaurant offering up delicious tapas, and is the sister of the famous Oleana restaurant in Cambridge. We went to both for research purposes, and I have to say, I preferred Sarma. Oleana was beautiful, but Sarma has more character. Definitely better for a younger crowd!

The decor is bright and colorful, with a great bar and a few communal spots. In addition to the regular menu, servers come around with various tapas to grab right from their tray, dim sum style. 

State Park in Cambridge

State Park is a great bar in Cambridge with pool, shuffleboard, pinball, duck hunter, and cheap drinks. It had a really cool vibe. Highly recommend heading here for a few beverages! Ask your uber driver to drive through MIT on your way home to check out the campus. The modern architecture will blow your mind.

Really makes you question your life choices while eating pizza drunk in the back of an uber driving through the campus knowing some of the smartest humans alive have attended this school but hey, to each their own. 

Day 3 of 3 days in Boston

You’re on the home stretch!

Take this day at a more leisurely pace. Grab breakfast at either Stephanie’s or Tatte Bakery and head to Isabella Stewart Gardner Museum.

Isabella Stewart Gardner Museum

This was one of the coolest places we went to in Boston. A collector of art through the ages, Isabella Stewart Gardner donated her entire collection to the city of Boston to display for the world to see after her passing. Walk around … and obviously take a few snaps for instagram because I mean:

Dinner before Boston Red Sox Game

Hit up Tapestry for pizza or Hojoko (in the Verb hotel) for bites before the game. If you’re a fan of negroni’s, order one at Hojoko! They are heavenly.

Check out my post on the best restaurants near Fenway to decide where you’d like to eat, as there are a plethora of great options before heading to the park.

Fenway Park for Boston Red Sox Game

You really can’t take a trip to Boston without visiting Fenway Park. Hopefully, your trip coincides with a game or two, because the Boston experience isn’t complete without a monster dog and cold beer at Fenway. Take in the energy of this iconic baseball park, sing Sweet Caroline at the top of your lungs, and try your hand at starting a “YANKEE’S SUCK!” chant like a true Sox fan.

3 Days in Boston isn’t enough time to really experience what this magical city has to offer, but it’s a great start. Boston stole my heart, and I can’t wait to go back. The locals are so friendly, the food and nightlife scene is vibrant and energetic, and history makes it easy to spend all day exploring a new corner of the city. 

Been to Boston? Let me know if you visit any of these places and tell me what you think!

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