How to Spend Four Iconic Days in Boston

boston travel tips

Boston is rich with history, culture, cuisine, and entertainment, and should be merited four days, at least, with which to explore its offerings. One or two days is plenty of time to explore certain destinations, but trust us when we recommend four for Boston.

Each neighborhood within Boston has its own unique personality and restaurants to try. With more universities per square mile than anywhere else, a massive part of Boston’s culture is learning and education, which is also represented by the array of incredible museums throughout the city. Four days in Boston means four days of delicious cuisine, seeing the world through a new lens, celebrating the history of our nation, and enjoying the ambiance of a city both young an old.

Boston Travel Tips – Here’s Your 4-Day Itinerary!

Day One: The Freedom Trail

One of the best ways to get to see many of Boston’s icons in one fell swoop is by walking the Freedom Trail. The Trail winds between 16 historically significant sites over the course of 2.5 miles, and is marked by a red line the entire way. You’ll be walking in the steps of America’s founding fathers, guided by yourselves, or if you prefer, a guided tour. There are a variety of guided tours with different themes; there’s even a historic pub crawl tour! You can view them all here. If you have the entire day to spend here, a great spot for lunch and shopping is Quincy Market and Faneuil Hall, also iconic sites not to be missed!

If you opted to do the Freedom Trail after lunch, you’ll have worked up an appetite again just in time to have dinner at Stephanie’s, a Boston favorite since 1994.

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boston travel tips

Day Two: The Back Bay

Often, when people think of Boston images of beautiful architecture and classic brownstone homes come to mind. Few neighborhoods within Boston exemplify the spirit and aesthetic of Boston more than Copley Square and Beacon Hill, two areas set within Boston’s famed Back Back. We recommend dedicating an entire day to enjoying all this area has to offer. Plus, if you’re staying at Copley Square Hotel, you’ll already be staying in the Back Bay and can easily walk to all of the sites!

We recommend planning an itinerary with these sites and experiences woven in:

Boston Public Library – Take a guided tour, or grab a coffee and pasty inside and sit in the lovely open-air courtyard.

Copley Square – A charming and extremely historic square within Boston featuring the Old South Church and Trinity Church.

Lunch at Eataly – Step out of Boston and into Italy. Eataly is an Italian marketplace and dining mecca. This is not something to be missed, and it’s steps away from the library.

Boston Common + Public Garden – Stroll through the common people-watching until you reach the Public Garden and then hop aboard a Swan Boat.

Beacon Hill – Ahhh, Beacon Hill is an absolute treasure. A hilly neighborhood with spectacular architecture, brick roads, charming coffee shops, delicious restaurants, and fun shops. This could be your sunset destination; Beacon Hill draped in dusk light is magical.

Once again, your appetite will have been thoroughly worked up, and the place where we recommend you satiate your palate is 75 Chestnut. Both cozy and elegant, this Amerian eatery offers delicious cuisine with plenty of vegan and vegetarian-friendly options. The ambiance and aesthetic are second-to-none.

RELATED: Things You Didn’t Know About Boston’s Iconic Swan Boats -Hint, Knights and Princesses Were Involved

boston travel tips

Day Three: Boston Harbor

Out of all Boston, perhaps the most famous, and infamous, is the Boston Harbor. Yes, the site where loads of tea was dumped into the ocean and the seeds of rebellion against Britain were sown. Sites we recommend seeing on this day include:

Boston Tea Party Ships & Museum – Discover how the Boston Tea Party happened, you can even watch a reenactment.

Stroll along the Esplanade – All along the Charles River is a lovely pathway and park filled with people running, biking, picnicking, and enjoying the city. This is also a great spot to picnic!

Visit the Aquarium – Get up close and personal with the creatures of the sea at one of the nation’s most acclaimed aquariums.

Museum of Science – One of the top museums within Boston, be sure not to miss the exhibit on Outer Space!

For the evening portion of your day, how about dinner and a show? Boston has a magnificent array of artistic talent; everything from ballet to stand up comedy. Peruse the offerings at:

Boston Ballet

Boston Opera House

Charles Playhouse

Or refer to this guide to see every possible option! For the dinner portion, it will depend on which part of town your evening entertainment will be in, but one of our go-to pre-show dinner spots is Top of the Hub, the restaurant at the top of the Prudential Center. High above Boston, the twinkling lights of the city will leave you feeling exhilarated and glad to be alive!

red sox and fenway park

Day Four: Fenway Park + Isabella Stewart Gardner Museum

Oh, there simply aren’t enough days to see and experience all of Boston, guess you’ll have to come back again! On your final day, depending on how much time you have we recommend filling it with the following sites:

Fenway Park – No trip to Boston is truly complete without either seeing a game at Fenway Park or taking a tour. There’s so much history involved with Fenway Park, and it’s part of the heart and soul of the city.

The Isabella Stewart Gardner Museum – One of the most spectacular museums in the entire country, you can easily spend hours getting lost among the extensive collections of art and finery on display here.

You don’t want to leave the city without eating at a classic Irish pub, another piece of Boston culture to enjoy. There are many to choose from, but one of the best, and not too far from Fenway Park, is Solas Irish Pub.

As mentioned, there’s no end to the entertainment and excitement to enjoy throughout Boston. If you decide to spend more than four days and want further recommendations, connect with us! We love helping guests build itineraries to see as much of our amazing city as possible. If you have not yet booked your accommodations, we recommend doing so ASAP! The city gets busy throughout spring, over summer, and even into early fall. Happy planning!

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