Are you planning a quick trip to the City on a Hill? If you are looking for how to spend one day in Boston, we’ve got you covered here with a great itinerary for 24 hours of Boston fun!
Of course, there are so many fun things to do and see in Boston that for optimal Boston fun, adding even one more day to your visit in this wicked cool New England city would double your fun, but if you’ve only got one day, let’s make it count!
A quick note about getting around the city: drive if you must, but parking is limited in many popular spots, driving around the narrow, historic roads searching for a parking spot eats up some of your precious fun in Boston time, and paying for parking will quickly add up! Uber, Lyft, and the “T” can get you anywhere you’d like to go during your 24 hours in Boston; most of the 24-hour Boston itinerary below is designed to be walkable!
Okay, you’ve got one day in Boston: Here’s how you can have 24 hours of Boston fun!
Fuel Up at North End’s Caffe Lil Italy
You certainly won’t go wrong starting off your day in Boston at any one of Boston’s fantastic coffee shops, but Caffe Lil Italy is an authentic Italian cafe in Boston’s North End neighborhood that serves up traditional Italian delights like cannoli and espresso that are oh so delizioso! Whether you’re getting a ride there or driving yourself, be sure to pass by the Skinny House/Spite House on the way, it’s less than 500ft away from Caffe Lil Italy on Hull St. Enjoy your breakfast either indoors or out on the patio before you head off on foot to your next stop!
Hop on the Boston Freedom Trail!
Guess what is directly across the street from Caffee Lil Italy? Old North Church, of Paul Revere’s Midnight Ride fame! Follow the red brick underfoot to continue on through Paul Revere Mall, past the Paul Revere statue, to the Paul Revere House, downtown Boston’s oldest building! You’re technically traveling the Freedom Trail “backward,” but that’s no problem. You’ve only got one day in Boston, we’re working against the clock here!
Walk on to get to Historic Faneuil Hall, “the cradle of liberty,” and get some pics of the golden grasshopper weathervane perched on top! Continue on and you’ll see the Boston Massacre Site, the Old State House, and more on your way to Boston Common, America’s oldest park.
Home to Frog Pond, the iconic Boston pond that transforms from a splash pad in the summer to an ice skating rink in the winter, Boston Common is also full of historic monuments and memorials, so wander around a bit checking out plaques and statues! If it’s hot out during your day in Boston, cool off in Frog Pond. If it’s iced over, rent some skates and take a spin on this famous outdoor ice skating rink! Often called “The People’s Park,” Boston Common hosts events all throughout the year, so chances are good that something interesting will be happening in the park during your visit!
Head to Boston Public Garden
Okay, you’ve walked a big chunk of the Boston Freedom Trail and experienced Boston Common, now what? Luckily, all you have to do is cross the street to visit Boston’s other most famous park, Boston Public Garden. Take a selfie or two with the Make Way for Ducklings sculpture before heading to the iconic swan boats! Operating April through September, the Swan Boat Cruise is a must-do on any visit to Boston; it’s only a 15-minute ride, too, so there’s definitely time to fit in a Swan Boat ride on your one day trip to Boston!
Grab a Bite & a Brew
You’ve probably worked up a bit of an appetite by now, and lucky for you, Boston is a city that can take care of that! There are plenty of fun and unique restaurants for just about anything you’re in the mood for, whether you’re looking for vegetarian options, Boston breweries, or a classic Irish pub! The iconic Cheers bar and restaurant is located just across the street from the Public Garden if you’d like a side of 80s and 90s sitcom nostalgia along with your meal.
Calling All Sports Fans!
Boston is home to Fenway Park, “America’s Most Beloved Ballpark,” so if you’re a baseball fan, swing by this famous sports institution while in the area! Guided tours of Fenway Park are only 40 minutes long and run every day of the week, year-round, with the last tour departing three hours before game time on game days, so if you are a sports fan, consider signing up for a guided tour of this American sports institution! You can easily get to Fenway Park by grabbing a ride on the Green Line from Boston Common, too.
So Many Museums, So Little Time…
Boston is home to a lot of incredible museums and great educational walking tours, but if you’ve only got one day in Boston, you’ve got some hard choices to make! Luckily, some of the coolest museums Boston has to offer are near each other and only a quick 15-minute walk over from Fenway Park, too! Consider the Isabella Stewart Gardner Museum, Museum of Fine Arts, MassArt Art Museum, or, if you’d prefer an aquarium over a museum, the New England Aquarium is always a great choice, but you’ll need to Uber, Lyft, or catch the tram near the Museum of Fine Arts to the Government Center to ride the Blue Line all the way to the New England Aquarium!
Take to the Water
Taking a cruise out on the Boston Harbor is a fantastic way to take in the beauty of this waterfront city! Just a few steps from the New England Aquarium, board a Sunset Cruise and kick back with your favorite drink as you tour the Harbor Islands and important historical sites. On this fully narrated tour, you’ll learn even more reasons to love this historic city as you witness the iconic Boston skyline glow with the golden hues of the setting sun! Bonus points if you’re traveling with a romantic partner, because a sunset cruise on the harbor is wicked romantic.
Figure Out Your Landing Spot
Boston is full of cool Airbnbs and interesting hotels, so you’ve got plenty of options! If you’re looking to stay somewhere one of a kind, check out The Liberty Hotel in Beacon Hill, the boutique hotel with a checkered past! Formerly Charles Street Jail from 1851-1990, you’ll find playful nods to its past throughout this unique Boston hotel! Plus, a stay at The Liberty means you’re within walking distance of lots of shopping, restaurants, and cool things to do, so maybe after you’ve grabbed some dinner, you might walk the Charles River Esplanade and see if there are any events happening at the Hatch Shell, the outdoor music venue!
Dinner & Nightlife
Again, there is no shortage of great food and drink options in the City on a Hill! If you’re looking for a night of laughs, consider checking out one of Boston’s comedy clubs, or if it’s theater you’re in the mood for, see what shows are happening around town! If it’s trendy, popular dinner spots you’re after, follow the cool kids to some of Boston’s hippest restaurants. If you just need to get your groove on, you’ll find a vibrant nightclub scene in Boston, too! Whatever way you’re looking to endcap your one day in Boston, it’s there!
Boston is a great place to visit anytime of year, but each season holds its charm. Winter may be cold, but there are lots of fun winter things to do, and Christmas time is downright magic. Spring in Boston is absolutely gorgeous, and no one does St Patricks Day like Boston! Summer is hot but that doesn’t slow Boston down, and fall in Boston is a symphony of vibrant fall color, and if you’re into spooky fun like ghost tours, Boston has plenty of that too!
Whether you’ve only got one day in Boston or you decide to make it a weekend trip, check out the Go Boston Card and the Boston CityPASS for discounted entry and access to some of Boston’s most popular sites. Have fun on your one day in Boston!
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Amy is the founder of New England with love. A proud Vermonter, she hopes to share her love of New England and help you find the best adventures in the region. Amy is also blogger/founder at Two Drifters, where she writes alongside her husband about romantic and couples travel, relationships, honeymoons, and more. When not working on websites, Amy is probably reading, cuddling with her husband, son, and cats, & drinking a maple latte.