Itineraries for Your Trip to Boston
2 Days in Boston for First Timers
I didn’t fall in love instantly with Boston—it took moving out West and coming back to visit yearly to appreciate the city’s charms. There’s a European-like quality to parts of Boston that I’ve grown fond of, particularly in the North End, plus ocean views and an abundance of activities to pursue.
If you’re in Boston for two days, you have time to see the city’s highlights, learn about its history, and even come to understand some of its culture. From walking the Freedom Trail to sampling local eats, seeing the city from the water, and more, here is how to spend two days in Boston.
Boston’s seasons are extreme—summers can be punishingly humid and winters bitterly cold, so come prepared.
If you only get to do one thing, make it the Freedom Trail.
In the morning, head to the Boston Common to get on the Freedom Trail as you learn about Boston’s important role in the Revolutionary War. This 2.5-mile (4-kilometer) path through the city stops at historically significant sites that blend seamlessly into the modern cityscape. The Freedom Trail is best done on foot, but there are also bus versions for those who prefer them.
You’ll finish the Freedom Trail on Copp's Hill Terrace, and from there, you can wander cobblestone alleyways through the Italian North End neighborhood, one of the best places for a meal in all of Boston. On a food tour, you’ll sample everything from classic Italian fare to typical New England dishes like lobster rolls and clam chowder as you learn about Boston’s culinary history.
If you haven’t fallen for Boston yet, a sunset cruise around the Boston Harbor should seal the deal. You can reach the harbor via the city’s subway (called the "T” by locals), then hop on a boat to admire the skyline set against the backdrop of the setting sun. Make sure to listen for the cannonball fired by the USS Constitution every night around this time.
Boston is well-known for its sports teams, and perhaps none so much as the Red Sox. In the morning, tour Fenway Park, a stadium known and loved by Red Sox fans and non-fans alike. Learn about the stadium’s history (did you know it’s more than 100 years old?) and some of the most famous players to have set foot on the field, then check out the on-site museum.
It’s a lovely walk from Fenway back into Boston, passing by the Fenway Garden Society’s community garden and the James P. Kelleher Rose Garden before you reach the neighborhood near Northeastern University. After a bite to eat, visit the Museum of Fine Arts, Boston, with its collection of more than 500,000 works. How long you spend in the museum is up to you—it can be a quick visit or an all-day affair.
On your last night in Boston, get a taste of local nightlife by visiting neighborhoods like the South End or Downtown, where interesting bars and restaurants abound. While you’re in the heart of the city, head up to the Boston Observation Deck for 360-degree views. The Prudential Tower’s 52nd floor features a rooftop cocktail lounge, the perfect place for a drink at sunset.
