Updated July 21, 2020.

So you only have one day in Boston? Not sure how you could possibly fit it all in? Never fear! I have your ultimate one day guide to historic Boston whether you’re in town on business, squeezing in some sight-seeing on a college visit, or just need a change of scenery for a day! Times are suggestions only. Have so much fun!

***Note: If you’d like to try the original Boston Cream Pie and eat an authentic Parker House Roll, call or stop by the Omni Parker House (right next to the Freedom Trail at School and Tremont Streets) to ask whether you’ll need a reservation for dinner. If so, make your reservation for 5:00pm, 5:30pm, or 6:00pm to beat the later dinner rush.

Stop 1, 9:00am: Tour Fenway Park (10:00am in winter)

Ticket price $20; subject to change

Grab breakfast at your hotel or at one of the many coffee shops on practically every street in downtown Boston, and then take the T to Fenway! The first tour starts at 9:00am  April 1-October 31, and 10:00am November 1-March 31. While Fenway Park is not as old as some other sites in Boston, some would argue it’s just as historic! Baseball is America’s pastime, after all, and this is the oldest baseball staduim still in use!

Stop 2, 10:30am: Pick and Choose on the Freedom Trail

Trail is FREE, some individual sites charge admission—prices vary

You may already know what sites you definitely want to see on the Freedom Trail, but if not, I’ve outlined them (with current prices!) in Your Guide to Boston’s Freedom Trail! I suggest staying in Boston proper and not crossing the bridge, as this will cut into your day quite significantly. There are some guided tours you can take, but the trail is easy to follow on your own, too! You should have plenty to cover all the sites from Boston Common to Copp’s Hill Burying Ground in about 2-2.5 hours if you like, or just choose 3-4 sites and spend about an hour and a half really digging into those. My favorites are the Old South Meeting House, the Old State House, Faneuil Hall, and the Old North Church!

More here: Your Ultimate Guide to the Freedom Trail

Stop 3, 1:00pm: Lunch at Quincy Market or choose a pub at Union and Marshall Streets

Option 1: You’ll be needing to refuel around noon or so, and you’ll find just about anything you could want inside Quincy Market! It will likely be crowded, and you may have to go outside to find a place to sit, but you’ll be satisfied with what you get! Lobster rolls are always a winner, but on cooler days you can get lobster bisque or clam chowder (or pizza and sandwiches if seafood is not your thing!); if you’re craving something sweet you’ll find chocolate-covered everything, ice cream, or cookies of all sorts; and if you just need some refreshment, there are juices, teas, soft drinks, water, and more!

Option 2: Not hungry by the time you get to Quincy? Prefer a pub full of history instead? Check out any of the pubs on the Freedom Trail at Union and Marshall Streets. The Bell in Hand, Union Oyster House, and the Green Dragon Tavern are all great options where eighteenth century Bostonians used to debate the great issues of the day!

Hungry for more? What to Eat in Boston

Stop 4, 2:00pm: Boston Tea Party Ships and Museum ($30) or USS Constitution

Ship admission is FREE; $10-15 donation requested at museum

Option 1: Once you’ve filled up, start walking toward the Boston Tea Party Ships and Museum (or Uber if you’re already tired of walking!). This is not included on the Freedom Trail, but it has been voted the #1 museum in Boston! You can see the only known surviving tea chest from the “tea party,” tour the ships, and even throw some tea overboard if you feel like it!

Option 2: Take a short walk down to the aquarium wharf and take the water shuttle from there to the USS Constitution and Museum! This will save your feet and your time, and if you really want to complete the Freedom Trail, this is the best way to do it in a day! The shuttle takes 8 minutes and costs only $3.50, and it drops you off only a few yards from the Old Ironsides and the museum.

Stop 5, 6:00pm: Dinner at The Parker House Restaurant

Call ahead to find out if you need a reservation for your trip date.

You can’t say you’ve had an historic day in Boston without trying the original Boston Cream Pie—it can’t be done! So plan to have dinner at the Omni Parker House Hotel Restaurant. This is where it was invented, and they still serve it today. Parker House Rolls were also invented here and will come with your meal (save one to dip into their clam chowder).

Restaurant full? You can still pick up an original Boston Cream Pie in their shop downstairs!

Looking for a place to stay that steeped with history and has been painstakingly preserved? I can personally recommend the Omni Parker House. They did not give me a room for free or pay me to type that. It really is a beautiful, historic hotel! Be sure to explore the hallways downstairs to see artifacts and mementos from famous patrons past, such as President Lincoln, President Kennedy, and Charles Dickens!

Add-on Option 1: Boston Common and Public Garden

Are you an early riser? A morning stroll through historic Boston Common and its across-the-street neighbor, the Public Garden, will certainly start your day on the right foot! Interested in taking a Swan Boat ride (run by the same family for over 100 years!)? Come back in the afternoon for a float around the pond!

More here: What to Know Before You Visit Boston

Add-on Option 2: Take a Tour

Got a little more time? Take a tour! My running tour with Run Boston was fantastic, but there are also walking tours, ghost tours, and more to choose from! Just do a quick Internet search or tap around on the Trip Advisor app to find the one that’s best for you!

Are you ready to take on one fun-filled day in Boston? Tell me below! And while you’re at it, check out my United States Page for everything you need and more about Boston and beyond!

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