We know winter in Boston can get a little cold, but that doesn’t mean the fun has to stop! From cozy dining to immersive experiences, sing-your-heart-out-worthy concerts to award-winning performing arts, and cherished neighborhood gems to iconic outdoor activities, there's something for everyone in Boston during the colder months.   

Continue reading for our guide to the perfect three-day winter itinerary in Boston.  

 

 

Day One

Check into one of Boston’s Cozy Hotels 

No winter getaway to Boston is complete without the coziest hotel stay. And, with over 140 lodging options within the Greater Boston region, including ones with fireplaces, winter experiences, and intimate hotel bars, there's a stay for every preference and budget. Find the perfect hotel here!

 

Explore Local Shops and Bookstores 

Once you've checked into your hotel, kick off your first day in Boston by shopping at the boutiques on Newbury Street, Charles Street, or the many main streets located throughout our 23 neighborhoods. Don't miss stops at some of Boston’s most unique bookstores such as Brattle Book Shop, Beacon Hill Books & Café, Harvard Bookstore, and Parkside Bookshop. Still in the mood to shop after these boutiques close? Stop by the Prudential Center for an elevated shopping experience at popular designer stores.

 

Have Dinner in Boston’s Historic North End 

After a day of shopping head to Boston’s North End to indulge in some of the city's best Italian food. One of Boston's most iconic foodie destinations, this historic Italian neighborhood is a staple for visitors and locals alike. Whether you're searching for Boston's best chicken parmesan and espresso martini or cooking that reminds you of your Nonna while away from home, this neighborhood is a must. 

 

End The night at one of the city’s activity bars

Hit the links at Five Iron Golf or Puttshack, catch a film at Alamo Drafthouse, play darts at Flight Club, go bowling at Kings or Lucky Strike, or experience the thrill of professional racing at F1 Arcade.  

 

 

Day Two

Grab Coffee or Breakfast at a Local Cafe 

Start your second day in Boston at a cozy neighborhood joint for coffee and breakfast. We recommend checking out spots like Cicada in Cambridge, Phin Coffee House in Downtown, Ula Café in Jamaica Plain, 3 Little Figs in Somerville, or Polcaris or Modern Bakery in the North End. Smaller coffeehouse chains like Blank Street Coffee, Tatte Bakery, and Flour Bakery + Cafe have multiple locations throughout the city and are also perfect places to jumpstart your day.

 

Visit an Immersive or Art Museum 

Next, head to one of Boston’s immersive museums such as the WNDR MuseumMuseum of Ice Cream, or the Museum of Illusions. For a more traditional (and just as fun!) experience, check out one of the city’s renowned art museums like the Museum of Fine ArtsHarvard Art MuseumsInstitute of Contemporary Art, or the Isabella Stewart Gardner Museum.  

 

Warm Up with Lunch in Boston’s Chinatown 

After a morning full of activity, visit Boston’s historic Chinatown neighborhood for a meal that's sure to warm up your day. Grab ramen at WakuWaku Ramen, Tora Ramen, or Ruckus, dumplings at Taiwan Cafe or Dumpling King, hotpot at Q Restaurant or Shabu Zen, or Dim Sum at Hei La Moon, Winsor Dim Sum Café, or Empire Garden Restaurant.  

 

Attend a Concert, Show, or Game 

After taking a break at your hotel, heat up your final night in Boston at a concert, a show, or by cheering on one of Boston's championship sports teams.

With a nightly lineup that ranges from local performers at a neighborhood jazz bar to the nation's top touring artist at a sold-out arena, chances are, Boston has an upcoming concert you'll love. See who's hitting the stages at Symphony HallMGM Music Hall, the House of BluesClub Passim, or TD Garden this winter.

In the mood for a show? Then see what's on at Boston's iconic playhouses like the Citizens Bank Opera HouseWang Theatre, or the Emerson Colonial Theatre. From touring Broadway hits hosted by Broadway in Boston and internationally acclaimed dance by Boston Ballet to productions and shows from smaller theatre companies, there is a show for everyone.  

Known as the City of Champions, there's always something to cheer for in Boston. Head to TD Garden for a Boston Celtics or Boston Bruins game. Don’t want to get tickets to the game, but want to join the fun? Then head to one of the city’s best sports bars and get in on the action.  

 

 

Day Three

Grab Brunch or High Tea 

Begin your last day with brunch at one of Boston’s cozy restaurants or a high tea experience at the Courtyard Restaurant at the Boston Public Library, Raffles Hotel, or Trifecta at the Four Seasons One Dalton.  

 

End with an Outdoor Adventure 

Just because it is winter doesn’t mean you have to be inside your entire trip! Experience winter wonder and explore one of Boston’s 2,300 acres of parks such as the Boston Public Garden or Rose Kennedy Greenway, or head to one of the city’s outdoor rinks for some fun on the ice.