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A Weekend in Boston – An Itinerary

How to Spend 48 Hours in Boston

Words by Teodora Burtescu

Boston is a perfect weekend getaway for any modern travelers that are passionate about politics or history, as it is the birthplace of the American Revolution, often being referred to as the “Cradle of Modern America”. Spend 48 unforgettable hours in this destination following our itinerary.



Breakfast at a local favorite

Start your trip with a hot cup of coffee at Thinking Cup on 165 Tremont St, and enjoy the wide variety of vegetarian, vegan, gluten-free, and dairy-free options. Begin your day with a treat from their vast selection of tasty pastries.

Explore the Boston Common

The Boston Common is the oldest public park in the United States. Established in 1634, its 50 acres are home to more than 600 different types of trees: a true oasis of serenity. You can also cross over to the nearby Boston Public Gardens and take a picture on the famous Good Will Hunting bench, featured in the iconic Robin Williams and Matt Damon Oscar-winning film.

Take a walk through history on the Freedom Trail

The Freedom Trail is a 2.5-mile route covering 16 of the most remarkable historical sites in Boston, such as the Old South Meeting House, Faneuil Hall, and the Massachusetts State House. Follow the red brick line running through the city and explore the story of the American Revolution like you’ve never seen it before. Explore the trail at your own pace and stop along the way to visit the attractions you find most interesting, or opt for a guided tour.

Try the original Boston cream pie

Make a short stop along your way at the Omni Park House, the oldest continuously operating hotel in the United States and the birthplace of the official Massachusetts dessert: the Boston Cream Pie. Enjoy this delicious treat in a venue that has previously hosted illustrious figures such as Charles Dickens or Nathaniel Hawthrone.


Lunch in Boston’s “Little Italy”

The trail terminates in the North End, Boston’s oldest neighborhood – also known as “Little Italy.” Enjoy the mixture of modern and historic buildings and don’t forget to snap a picture in front of Paul Revere’s house. If you’re finding it hard to choose from the wide selection of authentic restaurants, opt for one of the many pizza tours available.

Visit the Institute of Contemporary Art Boston

Unwind during a tour at the Institute of Contemporary Art Boston, taking in the innovative experimental exhibitions available. Founded in 1936, this is the sister institution of New York’s MoMA, the two having paved the way for museums of this type together.


Seafood dinner

Since Boston is often cited as America’s seafood capital, you simply have to end your first day in the city at James Hook & Co. The family-owned fishery has been delivering the highest quality lobster and seafood to countless clients in its nearly one century of activity. You can enjoy it all freshly prepared just for you, straight from Boston’s historic waterfront.



Breakfast at Flour Bakery

Apart from the fresh and delicious pastries it offers, Flour Bakery is also remarkable due to the special story behind its establishment. Joanne Chang, the owner and pastry chef of the chain, graduated from Harvard University with a degree in Applied Mathematics and Economics and decided to step away from the domain she had studied and follow her passion for baking. She now runs eight shops all across Boston and has received the James Beard Foundation Award for Outstanding Baker. A truly inspiring way to start your day.

Reenact a pivotal moment in history

Choose to experience history like you never have before. You can watch the events of the night of December 16, 1773, unfold right in front of your eyes, while also playing along at the Boston Tea Party Ship. You get assigned a role in the event that ignited the American Revolution – complete with a costume. Everything takes place on three ships that have been constructed as exact replicas of the originals, giving the experience a truly realistic feel. And the best part- you also get to fight against taxation without representation yourself by throwing the tea overboard on your own.


Have a classic Boston deli lunch

Grab lunch at Sam LaGrassa’s, a family-run shop renowned for its specialty sandwiches. Choose from the selection of world-famous Rumanian pastrami sandwiches, or opt for one of the many vegan/vegetarian options.

See Trinity Church – an Architectural Masterpiece

Start exploring the surrounding areas with a visit to Trinity Church, built by the famous American architect Henry Hobson Richardson. The church was built in Richardson’s own interpretation of the Romanesque tradition, creating an unparalleled design. It was named one of the “Ten Most Significant Buildings in the United States” by the American Institute of Architects, so you should definitely consider paying it a visit.

Stroll through the Boston Public Library

This is the third-largest public library in the United States, hosting over 23 million items. Here you can find anything and everything- from books and manuscripts to maps and electronic resources.

Catch a bird’s-eye view of Boston

The Skywalk Observatory offers an incredible 360-degree view of the city from its 50th floor. As your time in Boston approaches its end, get the last view of the places you have explored and see them from a completely new angle.


Dinner at Deuxave

Finish your city break on the right note at a select fine-dining restaurant. Situated in one of the most beautiful settings Boston has to offer, Deuxave’s grand windows overlook the Black Bay brownstones and the charming promenade of Commonwealth Avenue. Make sure to book in advance, as this is one of the most highly regarded French cuisine restaurants in the city. Enjoy a glass of great wine and start planning your next adventure.


Teodora Burtescu is a writer living in Durham. Teodora is deeply passionate about discovering new places and cultures.