Visiting Boston with teens? Traveling with teens can be interesting. A successful trip is dependent on a number of fickle factors: your teen’s interest in the destination, their attitude and mood on any given day, and their focus. (Are your teens always glued to their screens like mine are?) Traveling with multiple teens and tweens can be an even bigger challenge.
Whether your child enjoys sports, books, history, food or fashion, Boston as a family trip destination offers something for everyone.
The Sports Fanatic
For teens who love sports, Boston hits a homerun. The city includes an impressive line-up of iconic stadiums and teams – first and foremost being Fenway Park.
Baseball
Home to the Boston Red Sox, Fenway Park is the oldest stadium in Major League Baseball. Attend a game and view the 37 ft. high left field wall known as the “Green Monster” and witness one of the last hand-operated scoreboards in MLB. You’ll need to plan ahead, however. After winning the World Series in 2004, 2007, 2013, and 2018 Red Sox tickets can be hard to come by. If you aren’t going to a game, schedule a stadium tour, which are available year-round.
Basketball
NBA fans should make a fast break to watch the renowned Celtics compete at TD Garden – the sports arena that replaced the old Boston Garden. Winners of 17 NBA championships, the Celtics are the most successful franchise in the history of the NBA and have captivated crowds for decades.
Hockey
TD Garden is also home to the Boston Bruins. Teens will be thrilled watching exciting hockey action as the 6-time Stanley Cup winning Bruins take to the ice at their home games in the state-of-the-art arena – easily accessible right in downtown Boston’s north section.
Football
Just south of Boston in Foxborough, the New England Patriots play their home games at Gillette Stadium. Tied with the Steelers for the most Super Bowl wins (6 championships since 2002!) Patriot games are an exciting way to spend the day.
Soccer
Teens will get a kick out of watching New England’s Major League Soccer team – the New England Revolution. Under the same ownership as the New England Patriots, the Revs also play their home games at Gillette Stadium.
Lacrosse
Have a lacrosse enthusiast? Catch a home game as the Boston Cannons professional men’s lacrosse team takes on their rivals in nearby Quincy.
The History Buff
For teens who love history, Boston is the quintessential place to visit. Even to kids not fully sold on the idea of learning while on vacation, Boston can captivate their attention with its famous sites as well-known stories come to life.
The Freedom Trail
Most students in the U.S. have learned about Paul Revere and his midnight ride to warn the colonists of a British attack. Take your teen to where it all began as you tour Paul Revere’s house and the famous Old North Church in Boston. These are just two of the stops on the famed Freedom Trail – a 2.5 mile stretch running through Boston that entails 16 historic sites telling the story of the American Revolution. Walking the trail following the red line throughout town is very easy to navigate. Some of the other stops include: the site of the Boston Massacre, Old Statehouse, Granary Burying Ground, Bunker Hill Monument and the U.S.S. Constitution – a highlight for my teens and tween.
The oldest commissioned ship in the U.S. Navy, the U.S.S. Constitution or “Old Ironsides” as it is commonly called, fascinated us as we saw dozens of huge cannons aboard the ship and went below deck where it was easy to imagine sailors at war more than 200 years ago.
Even if you don’t experience all 16 stops on the Freedom Trail, some of the attractions are sure to interest your teen.
The Foodie
Boston is a haven for teens who love good food. (Isn’t that most of them?)
Little Italy
Stay in the North End, known as “Little Italy,” where there seems to be authentic Italian bakeries on every corner.
Then for lunch your teen can dive into some of the best tasting pizza they’ve ever eaten at Regina’s Pizzeria on Thacher Street. A fun dinnertime experience is fine dining at Dolce Vita Ristorante where your child will enjoy delicious plates of lasagna, ravioli, or other delectable dishes served up alongside a strolling accordion player – a favorite experience for my teens and tween.
If your teen is a bottomless pit like mine are, he’ll have no problem saving room for gelato or cannoli to top off the evening. Stroll down Hanover Street to Mike’s Pastry – famous for serving up one-of-a-kind cannoli and yummy gelato since 1946. If the line is too long at this wildly popular place, no worries, you’re only a few steps away from other great options: Modern Pastry, Caffé Vittoria and Caffé Paradiso are other popular places for after dinner desserts.
Seafood
If your teen needs a break from Italian pastry, pasta, and pizza you’re in luck. Boston’s fresh seafood options abound at many renowned places around town. Union Oyster House is the oldest continuously operating restaurant in America and a charming place to indulge in amazing oysters, clam chowder and lobster, among other scrumptious seafood platters. It was even a favorite dining spot for JFK who frequented the establishment and has a booth named after him.
The Bookworm
Teens who always have their nose in a book will appreciate the immense list of great authors who have called Boston home. Famed writers from long ago up to current day made their mark on Boston and the world, including literary greats Phillis Wheatley, Edgar Allan Poe, Louisa May Alcott, Oliver Wendell Holmes, Henry Wadsworth Longfellow, Robert Frost, Ralph Waldo Emerson, Sylvia Plath and Henry David Thoreau to name a few. 
Literary District
You can walk Boston’s Literary District – the area that celebrates Boston’s rich literary history with many literary landmarks and events. The list of stops is extensive so you’ll want to grab a map before you go. You can find one at http://bostonlitdistrict.org/map/
Here are just a few of the 85+ literary sites you can visit.
- Residences of Oliver Wendell Holmes, Nathaniel Hawthorne, Louisa May Alcott, Henry James, Robert Frost, and Sylvia Plath, among others. In fact, Hawthorne, Alcott and Thoreau all lived on the same block of Pinckney St. at some time in their lives.
- Edgar Allen Poe Square – A plaza near the birthplace of Edgar Allan Poe depicted by a sculpture of him with a raven perched on his shoulder and a heart coming out of his suitcase.
- Brattle Book Shop – one of America’s oldest booksellers. Located in a three-story building, the book shop carries more than 250,000 books, maps, prints, postcards and other items. Check out the third floor where you’ll find rare, signed and collectible books. Then head outside to find carts of books on sale.
- Old Corner Bookstore – The original bookstore building housed the publishing giant Ticknor and Fields. They produced such famous titles as The Scarlet Letter, Midnight Ride of Paul Revere, and other works by Alcott, Emerson and Harriet Beecher Stowe. The building is now commercially leased and actually stands as a Chipotle currently, so make this stop around mid-day and grab lunch on your tour!
- The Omni Parker House hotel where Emerson, Thoreau, Hawthorne and Longfellow regularly met for their legendary “Saturday Club.” It was also here where Charles Dickens gave a reading of A Christmas Carol.
- Boston Public Library – America’s first large free municipal library holds more than 23 million items, including first edition folios by William Shakespeare and the personal library of President John Adams. This is a can’t-miss experience just for the architecture of the building alone! The library offers free daily tours and hosts regular exhibitions and events as well.
The Fashionista
Whether your teen is into trendy, hip, high-end, classic, casual or funky fashion, Boston has a plethora of shopping opportunities. From upscale and unique boutiques to big commercial stores and even marketplace cart vendors, teens can load up on shoes, clothes, accessories, gifts and more.
Here are some of the shopping areas to check out with your teen:
Newbury Street
Upscale stores nestled amidst 19th century brownstones line this beautiful mile near Boston Common. It’s an expensive and elegant stretch, but worth a visit, even if just to window shop. You’ll find stores such as Burberry, Chanel and Diane von Furstenberg but also more affordable stores sprinkled in such as H&M and Nordstrom Rack.
Copley Place and Prudential Center
These two enclosed malls are connected by a glass skywalk providing a multitude of stores to choose from. Copley is a beautiful mall with marble columns, extra wide walkways and a huge rotunda. It contains high-end stores such as Barney’s, Louis Vuitton and Neiman Marcus. Prudential is more of a typical mall, where you’ll find Ann Taylor, Under Armour and White House Black Market.
Faneuil Hall Marketplace
One of the stops on the Freedom Trail, Faneuil Hall attracts 18 million visitors a year. Its historical buildings have been a prominent meeting place for centuries and it now encompasses an urban marketplace with more than 100 shops and vendors. Stores such as Urban Outfitters and Sephora are mixed in with dozens of places to pick up unique Boston souvenirs. Faneuil Hall also provides numerous restaurants and entertaining street performers – a definite must-do in Boston.
Harvard Square
Just across the river from Boston is Cambridge – home to Harvard University. Harvard Square is a unique shopping area with a diverse mix of stores. Funky or vintage, unique or university wear, you’ll find it all at Harvard Square – along with restaurants, coffee houses, music and street performers. A fun area for teens to spend the day.
Are you planning a trip to Boston with teens? What experience is your teen most looking forward to? Leave a comment below. We’d love to hear from you!
Want other teen-friendly destinations to venture to? Check out: Sedona with Teens and Family day trip to Savannah, Georgia, and Italy with Teens. Like it? Pin it and save for later!
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