Winter in Boston with the family may sound…well, cold. It ‘s true that the sun sets earlier, and you have to bundle up when you go out, because, New England! Even so, Boston an excellent city for a getaway with teens any time, and that includes winter.

There are plenty of fun places to keep you indoors — museums, movie theaters, and so many historical sites, of course. But Boston will also appeal to your kids’ love of shopping, eating, riding the T, and roaming the streets, which are all doable in the wintertime.

Just don’t forget your hat and scarf.

Here’s a snapshot of some of my favorite ideas from my own family’s winter trip to Boston last year. While some of our trip was spent touring colleges (Boston is home to 35 of them, which is another reason the city feels so youthful and vibrant), we also made time enjoy all the coolness of Boston.

Top photo: © Holly Rosen Fink for Cool Mom Picks


The Boston Neighborhoods: Where to Stay with Teens

Where to stay in Boston with Teens: Copley Plaza Hotel

The Copley Plaza Hotel is iconic

There are so many neighborhoods to choose from for a stay with teens in Boston, each with its own culture and community to explore, so here’s just a quick primer to give you the lay of the land, plus a few options to check out as far as hotels or inns.

Back Bay would always be my first suggestion for neighborhoods, because it really is the center of Boston and convenient to basically everything. It runs from essentially Mass Ave in the West to Arlington (where the Public Garden begins) in the East, and every street is full of charm. The Back Bay is home to Copley Square and the Boston Public Library as well as the wonderful shopping mecca, Newbury Street  (more below on that), the stately homes of Commonwealth Avenue (or Comm Ave as the locals call it), and great views of the Charles. There are plenty of great places to eat here in every price range, lots of cute coffee shops, and a terrific place to call home base.


Where to stay in Boston: The Newbury Guest HouseNewbury Guest House, via Trip Advisor

There are loads of options in the Back Bay — too many to even mention, so search for deals. If you want something “Old Boston,” look into the iconic Copley Plaza Hotel, The Boston Park Plaza, The Colonnade, or the Omni Parker House. The Lenox Hotel is right on Boylston, steps from Copley, and is a tried-and-true midsize hotel with old world charm, making it a favorite with visiting college parents. Also consider a small inn or townhouse, which function more like B&Bs and can offer terrific rates. Our editor Liz is a big fan of the Newbury Guest House (above) which could not be more central — it’s a brownstone smack in the center of Newbury Street! — and feels like a small European inn more than a bustling American hotel. The service is lovely if not five-star, and you can get some terrific deals.

Not far from there is Kenmore Square near Fenway Park and the Red Sox. It also marks the Eastern edge of the Boston University campus, and is right where the B train on the Green Line heads above ground, heading out of the city toward Boston College.

Just on the other side of Columbus from the Back Bay is the South End (not to be confused with South Boston), which isn’t packed with hotels, but that’s in part what makes it such a hip, young area. It’s very residential, fairly diverse (for Boston), and home to some of the best restaurants in town and tons of hidden boutiques. If you like staying more with locals than with other tourists its worth considering.

Beacon Hill is the charming area near Boston Common and the State House, full of gas lamps, boutiques, brownstones and restaurants. Especially if you love the idea of a cute Sunday brunch place. It’s not cheap, but it is delightful.

The North End, known as Boston’s Little Itlay, is another place to consider staying, especially if you’re traveling with young foodies. It’s right by the water front, central to the Quincy Market/Faneuil Hall area and the Seaport, and, the neighborhood has the distinction of being the city’s oldest residential community. That means it’s full of history– and as your kids will undoubtedly discover, great gelato.

Boston’s Seaport District/Waterfront s part of the Port of Boston on Boston Harbor and is home to the excellent Institute of Contemporary Art, the Boston Tea Party ship and museum, and Boston Children’s Museum. It’s been built up a ton over the past decade, but it’s mainly residential and fairly out-of-the way to most other neighborhoods, especially if you like staying in a walk-around area.

If you’re thinking the waterfront area, I’d suggest checking out the Seaport Hotel. It’s right near the Seaport Winter Village, where you’ll find a 3,000-foot ice-skating rink, great food, and winter treats for all ages including curling, and freshly baked waffles.your teens are big Instagrammers, take them to the Lawn on D in the Seaport District, where you’ll find swings that light up. It’s close to Tufts and the University School of Medicine. 

Downtown Boston/Financial District is a bit touristy and cramped, but certainly convenient to lots of the historic sites, like the Old State House and the Old South Meeting House, should you find any great deals on hotels there, It’s also the home to the pedestrian walking area called Downtown Crossing, where you’ll find tons of discount stores and street vendors, along with the bustle of the area’s financial workers. You probably won’t want to spend a lot time right in the neighborhood, so be aware that you’ll be on the T a lot.

Where to stay in Boston: The Royal Sonesta is right next to the Museum of ScienceThe Museum of Science, right next to the Royal Sonesta on the Cambridge side

Another option is to hop across the Charles River from Boston to CambridgeIt may be best known as the home of Harvard and MIT, but it’s a dynamic, fun, and fairly large city all on its own, filled with multiple neighborhoods each with distinct flavor. It’s great for young culture vultures with a rockin’ musical scene, a creative art culture, cool museums, and tons of multicultural dining.

I recently was invited by the Royal Sonesta Boston to stay the weekend as a press guest, and it was quite nice. It’s right across the river from the West End, in the Kendall Square neighborhood of Cambridge,  making it as easy to get toHarvard Square as it is to the Back Bay. It’s affordable for a larger hotel and surpprisingly cozy.  (In fact, most hotels are fairly cheap in the winter, which is another great reason to visit Boston on your winter break.)

The indoor heated pool has teen appeal, plus the rooms have an unbeatable view of the Boston skyline, which you can see at very top. It’s also next to the fantastic Museum of Science — so close you rarely see one photographed without the other — and I have to admit, being right across the street from a shopping mall os a total win with most teens.

Since it’s so easy to get around Boston on the T, you can really stay just about anywhere and find the whole city is accessible to you.


What to See and Do In Boston with Teens

What to do with teens in boston: The Old House State House on the Freedom Trail
Old House State House. Photo: Greater Boston Convention and Visitors Bureau

Boston is a great place to go with teens in the wintertime because, first, teens for some reason don’t seem to get as cold as we do when they’re having fun. And second,  there are just so many places, both inside and outside to keep us warm.

While some teens may be inclined to want to visit the many chain stores that they have in every other city (Urban Outfitters, Uniqlo, Starbucks you know the drill, parents) I’d say be sure to give some of Boston’s unique destinations some time in your itinerary. 

For example:

Brush Up on Historical Facts to the soundtrack of Hamilton

The best way to see the historical sights in Boston with teens is to walk down the Freedom Trail, a 2.5-mile path that takes you through the American Revolution through 16 sites. Great choices to stop include the Boston Common, Faneuil Hall Marketplace, the Paul Revere House, and the Old House State House, which commemorates the Boston Massacre. Belting the Hamilton tunes while roaming the streets made it so much more fun for us (yes, even though Hamilton takes place in New York City). Just be strategic about weather, and make sure to scout out good hot chocolate spots when you want to warm up along the way.


View this post on Instagram


A post shared by The Boston Common Frog Pond (@frogpondboston) on

You can also check out plenty of non-historical things there. Like go ice-skating in the Boston Common Frog Pond from November through March.It’s even open until 9PM, for a fun after-dinner treat if it’s not too freezing.

And feel free to check out the Cheers bar if you were a fan of the series in the 80s and 90s. (And of course your kids will have no idea what you’re talking about or why you’re there.) Just know that only the exterior looks like the place you remember, so don’t expect to find Sam Malone, Diane, or Woody inside. In fact, friends who know suggest just grabbing a picture outside and skipping the overpriced grub.

Eat your way through Faneuil Hall Marketplace

Speaking of food, you have to visit Faneuil Hall. The market is touristy, sure. But it’s also an amazing emporium of regional produce, dairy, seafood, and craft breweries. Steve’s Greek Cuisine, for example, serves up better Greek food than plenty of sit-down restaurants, which is why it’s endured for decades. Grab a gyro and scavenge for a seat in the center of the market, while local buskers play music and sing.

I also recommend Boston Chowda for traditional seafood chowder, which you kind of have to eat while you’re in Boston. It’s the law.  Pizzeria Regina is good for a decent slice of (inexpensive) pizza. and while there are lots of dessert options there for the kids to peruse, it’s hard to pass up Magnolia Bakery, and cupcakes as scrumptious as the ones from the original NYC location.


You can now do a Little Women scavenger hunt of locations when you take your teens to Boston!

Explore the Sites from The Little Women movie shoot

If your teens enjoyed Greta Gerwig’s film, they may love scouting out the Little Women locations using this digital map from the Mass Film Office which lets you turn your trip into a giant scavenger hunt. So cool!  Be sure to visit the Arnold Arboretum, Emerson Colonial Theatre Fairmont Copley Plaza, Gibson House Museum, and William Hickling Prescott House — all places you might recognize in the Marsh sisters’ many adventures.


What to do in Boston with teens: Visit the original Newbury Comics

Shop til you drop.

There’s great shopping all over Boston, including Cambridge, The South End, and Beacon Street, .But I’d start with  Newbury Street, the mile-long street (eight blocks) made up of gorgeous 19th-century brownstones, small boutiques, medium-sized chain stores, and restaurants.

You have to be sure to hit the original Newbury Comics, which is at the west end between Mass Ave and Hereford. It’s pop culture nirvana, packed with Funko Pop figures, cool t-shirts, silly gifts, and of course, comics galore. It’s a shell of its former indie self, for those of you who haven’t visited for years, but still fun for the kids.

My daughter’s favorite store, Urban Outfitters, is on Newbury, as is  Lush, Uniqlo, and Doc Marten. Her other two loves are Nordstrom Rack Newbury and Georgetown Cupcake. If you’re a chocolate fan, don’t miss the L.A. Burdick outpost on Clarendon Street, a CMP favorite. As you can probably guess, the shoppers are primarily students from surrounding universities.

In fact, let your kids roam around while you grab a coffee. You know how we all feel about giving older kids some alone time when we travel.

Ride the T!

Speaking of letting kids hang out by themselves, the T is not just an easy way to get around, it’s fun all on its own. Consider taking the B train of the Green line above ground, outbound. You’ll get a great view of Boston from Kenmore Square all the way out to Chestnut Hill, where Boston College is, which is quite gorgeous. All for just $2.25 with a Charlie Card. Then…head back to wherever you’re going next.

Spend time in Harvard Square

There are interesting shops, really great people watching, and lots of history here. Plus, it’s right near Harvard, so a visit may inspire your teens to reach for the stars in their college applications. (Ha. Or not.) If you want to get out of the cold, head to a film at the Brattle Theatre, a terrific repertory film house that’s been around since the 50s; you never know what movie you’ll be able to catch. Expect  options like a Godfather double feature, a discussion around The Day the Earth Stood Still, and maybe even a special guest or two.

The Hahvahd Tour is a unique take on a tour of Harvard University. Run by actual students who offer a few good stories of what it’s like to go to school there, their tours run several times each day year-round, and cost just $10 or less for students.

Head to a one of Boston’s many museums

Boston’s museums show off the city’s longtime affinity for history and art. At the Isabella Stewart Gardner Museum, there are gallery rooms filled with masterpieces collected from around the world, including frames of stolen artworks after a famous, still unsolved 1990 heist.  If you prefer more modern art, the Institute of Contemporary Art,or ICA, lets  teens learn about the work of ultra-modern artists with some cool film and multimedia exhibits as well.  At the Museum of Fine Arts, teens can enjoy relics and artifacts that will teach them about the history of Boston.

History fans are in luck, as you might imagine. The Boston Tea Party Ships & Museum celebrates the events of 1773 on the deck of an authentically restored tall ship, and while they think it might be goofy, it’s actually pretty cool .The John F. Kennedy Presidential Library and Museum were constructed to remember the life and achievements of Kennedy.

Located downtown, you might also check out The New England Holocaust Memorial, which is spectacular architecturally. It’s not a museum, but a memorial built to foster reflection on the impact of bigotry and the outcomes of evil during World War II and to this day. It’s an artful, dramatic experience and doesn’t take long.

Catch a touring show…cheap!

Boston has its share of great theater, with a fair amount of Broadway tours making there way here each year. There’s Mean Girls, Blue Man Group, Gloria: A Life, and coming soon, Fiddler on the Roof, and Matthew Broderick and Sarah Jessica Parker in Neil Simon’s Plaza Suite. Look for tickets at And if you want to grab tickets cheaper the day of show, you can do that too! Find Arts Boston booths in Copley Square and Faneuil Hall — and be sure to get there early, if you don’t want to wait outside long.

Take a Duck Tour. Don’t laugh. 

This famous sightseeing tour is more fun than you’d think, especially if you have a great guide, and give you a terrific chance to get an overview of Boston, with lots of trivia you might not otherwise know. It may even give you ideas for where to spend more time later. Just know it’s only open starting March 21, so while it may still feel like winter in Boston then, it is officially spring.

Eat your way through every neighborhood

This could be a post in itself so I’ll just highlight a few favorites here.

What to do with teens in Boston: Greenway Food Trucks and Custom House. Photo Credit: Kyle Klein.

Greenway Food Trucks and Custom House. Photo Credit: Kyle Klein.

I’d be neglectful if I didn’t mention those food trucks teens love so much — there are dozens parked around the Greenway public park. Teens love food trucks, and there are dozens floating around The Greenway. From Indian food and Korean fusion to fresh seafood and grilled cheese, there’s something for every palate. Plus, it’s pretty affordable! Check out the Food Truck Schedule for what’s there each day, year round.

In the North End, be sure to grab pasta, great pizza, or visit the wonderful bakeries selling cannoli and gelato. A few spots that we love include Al Dente, Antico Forno, and Bricco for pasta, pizza and a yummy breadbasket.

If your teens love Chinese food, Boston’s Chinatown is where you’ll find authentic dumplings, hot pot, dim sum, or if you’re craving something sweet, try red bean mooncakes and egg tarts. You’ll also find markets and shops full of Chinese delicacies and places to get bubble tea. The Q Restaurant is a good spot for Mongolian hot pots.

Pho Basil is just one of many, many great Back Bay restaurants, and if you’re into Vietnamese it’s worth a visit for Saigon noodles, drunken noodles and excellent pad Thai. It’s also worth what is frequently a long wait for a table. (Pro tip: Grab a soda at Wendy’s next door to get out of the cold.)

For something a little special, stop by the Langham Hotel for afternoon tea. It will get your teens out of the cold and warm you up with hot tea, scones with jam and clotted cream, and even hot chocolate with toasted marshmallows. It’s an experience! (Note: The hotel is currently under renovations and re-opens in summer of 2020.)

After a visit to the ICA or the Tea Party Museum, Gather is absolutely the best lunch in town. Order delicious, fresh food at the counter from soups to sandwiches to pastries, then enjoy at your leisure. Or if you’ve just come out of Mass MoCA,  Lickety Split is a family-owned cafe right next door, with excellent burritos, paninis, and a daily soup of the day. They make delicious homemade ice-cream, too.

And of course, there’s always Legal Seafood. Yes, it’s a chain now, but there’s still something so fun about going to where it all began. Besides, the lobstah is still fantastic, and have you really eaten in Boston until you’ve had lobster somewhere?