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Guide to Boston Sightseeing With Teens

Feb. 12, 2019
9 min read
Red Brick, Acorn Street, Boston, Massachusetts, America
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Teens -- they're just about the most difficult bunch to please. Between the eye rolls and constant phone checks, it’s hard to get a read on what activities teens would really love to participate on vacation. But Boston has plenty to offer even the most sullen young members of your family. TPG's picks are close to the city’s major universities so if you’re in town for a college tour, which feels like a necessary rite of passage these days, the teens in your family — and everybody else for matter — will really appreciate these welcome distractions. Even better, Boston is well connected by the city’s subway system, the T, which means your teen can even check off these sights independently and still be within close range.

Many family-friendly Boston points hotels also appeal to teens because of on-site pools, cool yet historical settings, waterfront locations or close access to trendy shopping areas. When you're ready to plan your Boston getaway, add these spots to your teen's sightseeing checklist:

Fairmont Copley Plaza (Image by Benji Stawski / The Points Guy)

Fenway Park

Close to Boston University, Fenway is affectionately called America’s Favorite Ballpark for good reason: It has oodles of old-fashioned charm and history is seeped in every stand of the historic sports venue. Boasting the iconic Green Monstah, Fenway Park is home to the city’s beloved Red Sox, who have won a fair number of World Series titles much to the delight of its adoring fans. Boston’s Green Monstah is so famous that it has spawned a series of creations modeled on the original, including the Green Monstah at Boston Burger Company.

You might spot the Cookie Monstah ice cream truck trundling along in the neighborhood, in which case try the Green Monstah ice cream sandwich (chocolate chunk cookies with green monster ice cream, i.e., mint Oreo) to complete the experience. You can catch a tour of Fenway where you can learn about the park’s history or even a game during the season, which typically runs March through October. Tours cost $21 for adults and $15 for kids 12 and under. Whatever you do, just don’t bring your Yankees hat along for the ride.

Fenway Park in Boston, MA. (Photo via Shutterstock)
Fenway Park (Photo via Shutterstock)

MIT Museum

If you’re in the area for a college tour, the MIT Museum is a must-see. Teens will appreciate the many rotating exhibitions and can easily spend a rainy afternoon or two exploring the museum’s extensive permanent collection of holograms. MIT is easily accessible via the city’s red line on the T and public transport is recommended as finding parking in Cambridge can often be challenging. The Kendall Square area, which houses the museum, is also packed with popular lunch spots, including Bon Me and The Toast Factory, so you can easily make a fun-packed afternoon out of your visit. Admission to the museum is free the last Sunday of each month, from September through June. Otherwise, admission is $10 for adults and $5 for seniors 65+ and kids aged 5–18. Children under 5 are free.

Paddle Up

One if by land, two if by sea? If land is too lame for your teens, they might love kayaking on the Charles, the river that separates Boston from Cambridge. The bonus: spectacular views of both skylines. Close to many area schools, including Boston University, MIT and Harvard, the Kendall Square location of Paddle Boston offers sunset tours, which allow even those who have never paddled before, to participate. Tickets for a two-hour guided tour plus rental a double kayak costs $49 for an adult and $45 for child ages 8 to 15. Paddle Boston also offers paddleboard tours from the same location. Weather permitting, tours are usually hosted from May through October.

Image courtesy of APCortizasJr / Getty Images

Skywalk Observatory

OK, it might not be Seattle’s Space Needle, but Boston boasts its own 360-degree views of the city from a majestic vantage point. The Skywalk Observatory, with audio tours outlining the city’s historical and cultural highlights, offered in a variety of languages, is great fun for teens as a way of capping off a busy day visiting area schools. Northeastern University is a few blocks away as is Berklee College of Music. The Skywalk is located above the Prudential Center, a popular shopping destination that is close to many of the city’s major hotels. Upscale shopping at Newbury Street nearby is an added draw as is the spectacular Boston Public Library, which is just a couple of blocks away. Adults cost $20, seniors 62+ and students with ID are $16 and kids 3–12 are $14. Students 3 and younger are free.

The Skywalk Observatory in Boston, MA. (Photo via Shutterstock)
The Skywalk Observatory (Photo via Shutterstock)

New England Aquarium

Located right on Boston's downtown Waterfront, the New England Aquarium is a beloved city landmark. Teens who are lucky enough to visit during popular feeding and cleaning times are in for an additional fun spectacle with the fish and/or penguins. The institution hosts a variety of rotating interactive exhibits and, from March to November, offers popular whale-watching tours. Boston’s famous Legal Sea Foods is located right next door to the aquarium so tongue-in-cheek teens can pop in here after a visit to make a meal out of Dory or Nemo’s cousin. There are a variety of ticket options that include just the aquarium or add on an IMAX movie or whale watch cruise in Boston Harbor. Tickets to the aquarium run about $28 for adults, $26 for seniors 60+, $19 for ages 3–11 and free for children under 3.

The New England Aquarium in Boston, MA. (Photo via Shutterstock)
New England Aquarium (Photo via Shutterstock)

Faneuil Hall Marketplace and Quincy Market

Close to Suffolk University, this is also a popular stop on Boston’s Freedom Trail, which winds its way around the city, stopping at major historical landmarks. Faneuil Hall, which has hosted many a famous speaker including Susan B. Anthony to Ted Kennedy, is known as the “Cradle of Liberty.” These days, the hall and neighboring marketplaces are home to many local artisans and a variety of dining options. Your teens can try authentic Boston clam “chowdah” as well as lobster rolls here. The cobblestone square outside Quincy Market sets the stage for an impressive rotating selection of street musicians and dancers who are bound to keep your teen engaged and excited.

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Faneuil Hall Marketplace in Boston, MA. (Photo via Shutterstock)
Faneuil Hall Marketplace (Photo via Shutterstock)

Lawn On D

Want to be a real hit with your teens? Bring them to one of Boston’s most Instagrammed attractions, the Lawn on D, located in the city’s tech hub: the Seaport District. The park includes a whole set of grown-up, tire-shaped swings that light up. Close to the Tufts University School of Medicine and the Convention Center, the park hosts many live events and community activities. Fun concessions also make this a hip place to visit in Beantown.


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Bottom Line

Boston is the place to take your teens to learn about American history and our country's diverse melting pot. In spring and summer, there are plenty of outdoor diversions and Boston's take on the holidays is second to none. Make a plan to spend some time in one of New England's most vibrant cities soon while using points at some family-friendly hotels (one of which was even a former jail -- sure to be a hit with teens).

Featured image by Getty Images