One Day in Boston Itinerary

Updated: November 23, 2023

If you are visiting Boston for the first time and have just one day, this itinerary will give you a great taste of what Boston is all about.

You will walk in the footsteps of the American Revolution, see landmark buildings, and go to a top museum.

You’ll even have time to get a panoramic view of the city and have a fun night out!

A big bonus: This itinerary is practically free!

You'll need money for food, a few rides on the very affordable public transportation system, and paid attractions, should you choose to go to one.

We are local tour guides who lead hundreds of visitors and locals each week through the streets of Boston on our pay-what-you-wish walking tours.

We've used our expertise and these experiences to help craft this one-day Boston itinerary.

Additionally, we considered the opinions and suggestions of the roughly 16k members of our popular Boston Travel Tips Facebook group.

Our group consists of locals, like our tour guides, who moderate the group, expats, regular visitors, as well as newbies to Boston.

You don't need to become a member to search for and read the posts, comments, and suggestions.

Check us out once you are finished reading this post.


MORNING

Your day will start by seeing some of the most significant places in American History by walking the Freedom Trail, a 2.5-mile long path that connects 16 historic sites.

You will see places like the Massachusetts State House, the Granary Burial Ground, Boston Common, Old South Meeting House, the Boston Massacre Site, and Paul Revere’s House.

If you’d like to visit these sites and learn about them with a local guide, join us for our 2-hour pay-what-you-wish guided walking tour of the Freedom Trail.

To explore on your own, you can use our Freedom Trail Map and Self-Guided Tour to find your way along the trail and learn about the stops along the way.

Another option is to take our GPS-enabled Audio Tour. Listen to a sample of our Freedom Trail Tour.

Take a pause in your journey at Faneuil Hall, to grab lunch at Quincy Market, part of the Faneuil Hall complex of four buildings.

Here you’ll find dozens of food stalls serving many types of cuisine and local specialties, like Boston Clam Chowder and "Boston Style" pizza.


AFTERNOON

After lunch, continue walking the Freedom Trail to the last two stops, the USS Constitution and Museum and the Bunker Hill Monument.

You can walk the entire way to these sites, or take public transportation via the MBTA Water Shuttle

It’s a short boat ride across the Charles River and at $3.25, it’s like a bargain scenic harbor cruise!

The USS Constitution

This permanently docked vessel was constructed according to the Naval Act of 1794 and was fundamental in helping America defeat the British in the War of 1812.

Tours are offered throughout the day and are pretty interesting.

If you are traveling with kids, this may just be the highlight of their day in Boston!

You can visit the ship year-round and admission to the ship is free. It’s one of the best free things to do in Boston.

See how to visit the USS Constitution and Museum.

Bunker Hill Monument

The Bunker Hill Monument is a 221-foot-tall granite obelisk marking the site of the first major battle of the American Revolution.

Besides witnessing a big piece of history, you can also get a good view of Boston from the top of the monument.

There’s also a nifty small museum at the base of the monument.

The monument and museum are free to visit and are open daily from 10 am to 5 pm, except Thanksgiving Day, Christmas Day, and New Year’s Day.

For more information, read our guide to the Bunker Hill Monument and Museum Guide

Before evening, you can fit in time to stop at one of the city’s many fine museums. Whatever your interest, there is a museum for you!

Better still many are free or offer free hours/days.

Read about these museums from our post, Free Museums in Boston.


NIGHT

Start your night by having delicious food in Boston's North End, the city's Little Italy.

Check out our post on places to eat in North End/Little Italy for recommendations from our local guides.

After dinner, we suggest one of the two activities below. One is free and the other requires you to buy a ticket.

If neither appeals to you, take a look at our post, Things to Do in Boston at Night for other ideas.


Option 1: Discover Beacon Hill

Stroll through Boston’s charming Beacon Hill.

Our 90-minute self-guided tour makes it easy for you to see the highlights of this neighborhood.

You could also take our GPS-led audio tour of Beacon Hill. Here's a sample.

If there is a crime buff in your group, you might like our pay-what-you-wish Beacon Hill Crime Tour, which runs several nights a week from April through October.


Option 2: Attend a Sports Game

If you are in town from April to October, spend your evening seeing the iconic Boston Red Sox play baseball at historic Fenway Park.

From October to April, you can see the Boston Celtics (basketball) and the Boston Bruins (ice hockey), and from September to January, the New England Patriots (football) all at other venues.

Your one day in Boston has come to an end, and we hope you enjoyed every minute of it!

If you are in town for more than one day, or decide after 24 hours that you simply must stay longer, check our extensive post, Things to Do in Boston, which includes a three-day itinerary.

TIP: Given the limited time you will have, another way to spend your time is to take a sightseeing tour. They are an ideal way to learn about a city in a short amount of time.

Below are some tours to consider


SIGHTSEEING TOURS

There are different types of tours to choose from and it depends on what you hope to get from your experience.

The walking tours are pay-what-you-wish but boat and bus tours do require a ticket.

To save on activities like this, consider looking into a tourist discount pass which we explain below.


Rundgänge

These tours allow you to see the city up close while locals share their first-hand insight and stories about the sites you will visit.

Free Tours by Foot offers several pay-what-you-wish guided walking tours of Boston.

See what tours we are offering here.

We also have several self-guided Boston tours that lead you to the locations we think are the most important places to visit in Boston but allow you to move at your own pace.

Our audio tours are another way to get to know the city. You pick the time, plug in your headphones and listen to one of our guides tell you about the sites you will see.


Bustouren

Boston Bus tours are a smart way to see a lot of the city in a short amount of time.

In Boston, you have a bunch of options.

Hop-On-Hop-Off tours are popular as are Duck Tours (amphibious vehicles).

There are also Night Tours and Ghost Bus Tours, as well as Boston TV and Movie Tours

Read about the various Boston Bus tours.


Boat Tours

Thanks to all the water surrounding Boston, there are many boat tours to choose from.

Sightseeing Boat Tours give you a nice overview of the city from the water.

Dining Cruises and Sunset Boat Tours are a relaxing way to spend the evening hours while getting great views of Boston from your boat.

For something different, take a cruise on a tall ship, which is a large sailboat of the kind you'd see in Boston Harbor in the 1600s!


TOURIST DISCOUNT PASSES

If you do plan to visit a paid attraction during your one day, you might want to look into purchasing a Boston tourist discount pass.

These passes bundle tickets for attractions and tours for one discounted price.

Check out our post on Boston discount tourist passes where we analyze and compare the various passes.


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About The Author

Brian Burgess

I was born in Cambridge and have been living in the Boston area all my life. I am a graduate of Boston's Emerson College with a degree in communications with a journalism/history focus. I have been leading tours for Free Tours By Foot Boston since it was started in the city of Boston in 2012, and enjoy sharing my knowledge of Boston's rich history with not only the guests on my tours, but with everyone I meet. <a href="https://freetoursbyfoot.com/contributors/brian-burgess/" Read More...
Updated: November 23rd, 2023
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