2 Day Itinerary Exploring Boston

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Advisor - Georgia Goddard
Curated By

Georgia Goddard

  • Boston

  • City Travel

  • Local Culture

  • Local Food

  • Sightseeing

A picture of a black-colored fountain surrounded by trees during the daytime.
Curator’s statement

Boston is a small city in the New England region of the United States. On a lot of people's bucket list, this adorable city full of history and stunning architecture is a must visit if you are on the east coast. I planned this two-day itinerary when i visited in the summer of 2023 and it worked perfectly, so I am sharing it to help you make the most of your city break as well!

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Day 1: Explore Cambridge, Beacon Hill and Boston Common

A wall of book shelves

Head over the Charles River to Cambridge to explore Harvard University. As the university has an open campus, you can walk around the grounds and take in the inspirational atmosphere. This New England town has a lovely feel to it, so take time to walk around the area and take a look at some of the shops. For lunch, head to Black Sheep Bagel Cafe to grab some coffee and a delicious bagel. Beware, they do run out of bagels as it is really popular, so don’t leave it too late!

Afterwards, head back to Boston and visit the Beacon Hill neighborhood. This residential and picturesque neighborhood is a great place to get a feel of the Boston lifestyle. Be sure to go into Beacon Hill Books & Cafe to explore the building and get some pictures.

Later on, take a stroll along Charles Street to Wen’s Noodle and Ramen to get some dinner. This Chinese restaurant offers authentic dishes in a relaxed environment. I recommend getting some of their dumplings as they are delicious! To end the say, walk through the Boston Common to Charles River Esplanade to watch the sunset. The setting is gorgeous and is the perfect place to reflect on a day of exploring.

Day 2: A Tour of History and Sports

A picture of the exterior structure of the Boston Public Library during daytime.

Begin you day in the Back Bay area and get some brunch at Saltie Girl. A chic restaurant that offers a range of great breakfast dishes and coffee in a beautiful decor. After you’ve enjoyed that, wonder around Newbury Street and have a look at the stalls and independent shops. Nearby is the Boston Public Library, which is free to enter. Its interior is stunning so make sure to go inside and into the gardens to get some pictures.

Next, head to the beginning of the Freedom Trail, a two-and-a-half mile-long path through Boston that passes by 17 locations significant to the history of the United States. The plaques and brickwork along the sidewalk make it easy to follow and see all the sights on the way. Following this, you should arrive at Quincy Market, home to various different eateries and stalls. Get some local food and head to the Christopher Columbus Waterfront Park to indulge and take in the views.

In the evening head to a sports game (make sure to check what is on depending on what season you visit.) Boston is home to many high regarded sports teams, so head to Fenway Park, home to the Boston Red Sox (MLB), Gilette Stadium, home to the New England Patriots (NFL), or to the ID Garden, home to the Boston Celtics (NBA). This is a great way to experience Boston’s culture and get involved like a local.

Need to know

Looking for more travel inspiration? Check out my guide, The Perfect 3 Day Itinerary for Your First Time in London.

This guide is part of our ongoing series on travel to Boston.

Advisor - Georgia Goddard

Travel Advisor

Georgia Goddard

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