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What to Do in Boston: A Three-Day Guide


What to do in Boston: A Three-Day Guide

7 min read – Boston – the “hub of the universe” – is one of the world’s greatest cities for a get away! Beantown is a history-buff’s paradise. The densely packed city is loaded with stunning landmarks, great restaurants & vibrant culture.

In short, Boston is one of the most unique cities in America and an amazing spot for a tourism trek.

So, if you’re going to spend a few days in Boston, where should you go? What should you do? Here’s a guide to spending three days in Beantown!


Boston Itinerary – Day 1

Explore the Museum of Fine Arts

What to do in Boston

On the first day in Boston, we’ll explore some of the most historic destinations and cultural attractions the city offers. Start at the beautiful Museum of Fine arts in Boston’s Longwood area. This incredible art museum is home to over 450,000 pieces of art, along with some remarkable special events, lectures, tours, studio art classes, and classic films. It’s a great way to start off any trek to Boston.


Lunch at the Union Oyster House

What to do in Boston - Union Oyster

On a day filled with history, it’s only worthy to grab lunch at America’s oldest restaurant. This charming, super-historic restaurant is a long-time Boston favorite for clam chowder, oysters, and other amazing seafood selections. If you’re there early enough, be sure to ask for the “Kennedy booth” – the preferred eating spot for JFK when he served as Senator for Massachusetts


The Freedom Trail

For our first day in Boston, we’re going to explore some of America’s most historic sights. Luckily, the good town of Boston has everything all marked out in the easy-to-walk Freedom Trail! On the Trail, you’ll start on the Boston Common and wind your way north, through the Massachusetts State House, Benjamin Franklin statue, Old State House, and Site of the Boston Massacre. From there, you’ll go into the North End at the Old North Church and then to the U.S.S. Constitution and Bunker Hill Monument in Charlestown. It’s a great way to see some of the great sights in the city.


Dinner at Tresca and dessert at Bova’s in the North End

Save some room for dinner in Boston’s incredible North End. A haven for some of the best Italian restaurants in the country, the North End is a vibrant, welcoming neighborhood with charm to spare. Try some of the classic Italian dishes at Tresca, an acclaimed restaurant co-owned by fabled Boston Bruins defenseman Ray Bourque. After dinner, grab a dessert pastry at Bova’s, the best bakery in the North End (avoid the long lines at Mike’s and Modern Pastry, the other two popular North End pastry destinations).


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Day 2

Take a Tour of Fenway Park

What to do in Boston - Fenway Park

What trip to Boston would be complete without a trip to Fenway? The tour of the ballpark is one of Boston’s best bargains. For a few bucks, you get an inside look at the ballpark and can even get a trip to the top of the Green Monster. Even Yankee fans are (begrudgingly) welcomed.


Grab Lunch at The Publick House

What to do in Boston - publick house

A short walk, subway trip, or Uber ride away from Fenway, The Publick House in Brookline is one of Boston’s coolest restaurants. This Belgian-inspired craft beer haven features one of the city’s greatest brew menus along with hearty favorites like mussels, cheeseburgers, and authentic French fries. The macaroni and cheese with five-cheese sauce is another must-have.


Stroll Through Newbury Street

After lunch, it’s time to head back into Boston along the city’s fabled Newbury Street. This extraordinary and lively street has a full range of excellent shops and wonderful restaurants and quiet bistros. Additionally, visitors can turn onto Boylston Street and walk the same route that serves as the finish line for the Boston Marathon.


Head to the JFK Library and Museum

Take the MBTA subway and the shuttle bus down to Columbia Point on the Red Line to stroll through the beautiful JFK Museum overlooking the Atlantic Ocean and explore the historic treasures within. The library, encompassing ten acres, provides insight into the life, leadership, and legacy of President Kennedy. The library highlights Kennedy’s enthusiasm for politics and public service, and illustrates the nature of the office of the President.  Right next door, there’s also the Edward M. Kennedy Institute for the United States Senate.


Dinner at the Tip Tap Room

For a unique dinner, how about a meal at Boston’s Tip Tap Room? This fun, funky restaurant includes a creative menu of wild game dishes and craft cocktails.


Day 3

Breakfast at The Neighborhood

Head out to Somerville and enjoy breakfast at the local favorite called “The Neighborhood.” Since 1983, this local institution is one of – if not the – best breakfast places in all of Boston. Fresh, homemade sauces and ingrediants combined with an authentic family atmosphere are not to be missed. Be sure to try some of their special Portuguese dishes, especially the house-favorite linguica.


Explore Harvard Square

Harvard square - what to do in Boston

From your Somerville expedition, take a quick walk over to Harvard Square to enjoy the beautiful campus and the various shops and restaurants around the school. Grab a drink or a bite to eat at a place like The Thirsty Scholar (where The Social Network was filmed), Grendel’s Den, or Charlie’s.


Dine at Alden and Harlow

Right below Cambridge’s celebrated Brattle Theatre, Alden and Harlow is one of the most stylish restaurants in town. Head in to grab the famous Alden and Harlow Burger or one of the restaurant’s craft cocktails for an exceptional dining experience.


Stroll Along the Charles River or Head to the Somerville Theatre

As we wind down our three days in Boston, there are a couple of great options for the last night in town! You could take a trip along the beautiful Charles River and head back into Boston. Or, head a little further back into Somerville and take in a show or a movie at the Somerville Theatre in Davis Square – a local favorite with a gorgeous, ornate main theater, balcony seats, and plenty of classics on the program. Either way, they’re great options to finish off three days in Boston!


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