Hi, my friends! After our last journey through Seattle in the Northwest and all over Texas down South, it’s time to swing back up to New England! If you’re a fan of American history, cannolis, and cobblestones, I’ve got the destination for you. Yup, it’s time for a fabulous weekend getaway in Boston, Massachusetts!

I’d recommend visiting in the spring or summer, or else be ready to face frigid wind and snow up to your knees! Otherwise, New York’s rival city, Beantown (yes, that’s a real nickname), is perfect for a weekend trip. You’ll have just enough attractions to fill up your itinerary, with enough space in between to grab brunch in the morning and drinks at night. 

Ready to bump shoulders with some Bostonians? Here’s my favorite itinerary for a weekend stay in Boston!

Before we get into what to do, let’s first cover one of the biggest decisions you’ll make, and that’s where to stay! I’ve lost count of how many times I’ve been to Boston, and I can confidently say that the Revolution Hotel is an absolute gem! It’s reasonably priced, trendy, and gives you the tiny home feel for a truly unique experience you’ll never forget.

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, I make a little bit of money if you click through and book. That being said, I would never recommend something to you that I don’t stand behind 100%.

Day 1: The Boston Common and the Freedom Trail

Good morning! Let’s grab some breakfast at The Paramount, where you can scarf down both standard decadent eggs and hash, or some Instagram-worthy avocado toast. After that, take a stroll around the lovely Beacon Hill neighborhood. With its redbrick mansions and cobblestone streets, you’ll feel transported back to the 1800s.  

Once you’ve gotten your fill, take an easy walk to the Boston Common, where we’ll be spending the rest of our morning! This is a gorgeous park at the heart of historical Boston that has been around since 1634. While you’re there, stroll through the Boston Public Garden with its steamy greenhouses, lagoon, and swan boats. 

Got your walking shoes on? Great! It’s time for the 2.5 mile Freedom Trail, which starts right here in the Boston Common and passes by such landmarks as Bunker Hill, the Old State House, Faneuil Hall, the Paul Revere House, and pretty much anything else an American History nerd could ever want! You can choose a variety of walking tours to embark on, from guided tours to more of a choose-your-own-adventure.

With that done, I’m betting your feet are getting sore. Mine sure was after my first time exploring everything I’d read about in my American History textbook! Depending on where you stopped off on the Freedom Trail, you can grab a cup of coffee at Caffe Ducali or Night Shift Brewing in the North End, or Ogawa Coffee near the Boston Tea Party Museum. 

To finish out the night, check out the Boston Harbor for a lovely stroll and a place to sit and enjoy the city’s Skyline at sunset. When you’re hungry for dinner, grab a bowl of classic New England clam chowder or a juicy lobster roll at Legal Seafoods – Harborside, a 20,000 square foot mammoth of a restaurant, complete with a rooftop cocktail lounge. Enjoy!

Day 2: Fenway and Back Bay

Our second day in Boston has a lazy start out in Back Bay, a trendy, high-end neighborhood with plenty more brunch options, like chique Krasi, or fancy French Mistral. What better way to start a Saturday than with mimosas and a nice eggs Benedict?

After you’ve brunched, take a walk along the Charles River Esplanade to digest, and gaze across the river at Cambridge, home of Harvard University and MIT. In this neighborhood, you’ll also find the gorgeous Boston Public Library, America’s first public library, and the lovely 19th-century Trinity Church. Art lovers can take this time to check out the Museum of Fine Arts.

Once you’re ready, mosey your way to Fenway Park, home of the Red Sox and America’s oldest ballpark. If you’ve made it during baseball season, the best time to visit is of course when there’s a home game, but never fear: there are plenty of tours available off-season! 

If you’re not much of a baseball fan, head to the Prudential Center Mall instead to find the lobby of the Skywalk Observatory. Grab a ticket and hop in the elevator to enjoy some of the best sightseeing in the city, from the highest floor in Boston!

After that, it’s time to grab dinner, and you simply cannot visit Boston without sampling some Italian food. There are some great options in Little Italy in the North End, but if you’d rather stay near Fenway, try out the highly-rated Mida or the dive bar atmosphere at Anchovies.

Day 3: Take It Slow Before You Go!

It’s the last day of our Boston weekend getaway! As I’ve said in other weekend itineraries, day three is the best time to take it slow and pick up any odds and ends in the city that you don’t want to leave behind.

Let’s start off with a leisurely walk around Faneuil Hall Marketplace and Quincy Market to find any last-minute souvenirs you’d like to take back with you. Be sure to visit nearby Mike’s Pastry for a box full of cannolis to store in your carry-on bag! My favorite is the classic with plain ricotta filling.

Go on a brewery tour to taste everything from Samuel Adams to BearMoose, or throw in a ghost tour for a spookier side of this historical town. After all that, you’ll have plenty of goodies and stories to share with the folks back home! I hope that you got a kick out of this 3-day Boston itinerary and that it gave you some great ideas for your upcoming weekend getaway! If you’re looking for a different destination, there are tons of other itineraries on my blog, like a weekend in Barcelona or Rome.

So many places to go and people to see! Happy travels, everybody.