A millennial’s guide to visiting Boston

Over Labor Day Weekend, my gal pals and I jetted off to Boston for a girls’ weekend. We looked forward to cooler temps (because Texas is HOT!), fresh seafood, historical sites and more fun. There’s so much to do, lots of rooftops to visit and a bunch of snaps to take. I’ve rounded up a few of my favorites below for readers to consider visiting if they’re headed up to New England.


Boston Commons

Boston Commons spans 50 acres and is the oldest park in the U.S. Come here for a picnic, and enjoy food trucks, including the famous Boston Cream Pie truck. Dozens of monuments and memorials are found throughout the park. Fun fact: The Freedom Trail path begins here. (Don’t forget to wear comfy shoes!)


Fenway Park


Whether or not you’re a Boston Red Sox fan, seeing Fenway Park was pretty neat (because I’m sports obsessed). This is the nation’s very first ballpark (just to add onto the city’s tremendous history!)


With all the walking around you’ll be doing, you are sure to be hungry. Stop by Wahlburger’s for burgers and brews afterward. You may recognize the name; it’s Mark Wahlburg and his family’s restaurant! The restaurant is just down the street from Fenway Park.


Skywalk Observatory

visiting boston via genpink.com

For a beautiful 360 view of the city, head to Prudential Center (50th floor) for access to the Skywalk Observatory. Admission is $19 per person, and student and group rates are also offered. I recommend coming here at night for an even more spectacular sight. Around the center, you can experience an audio tour and interactive exhibits to soak up more history facts about the city.

For dinner and drinks before or after your visit to the Skywalk Observatory, walk one block to Newberry Street. There, and along the way, are a ton of restaurants and bars.


Little Italy

Welcome to some of the best pizza and Italian food in the country! Little Italy, located in Boston’s North End, is a gorgeous, high-end neighborhood full of amazing food and rich history.


Even the cobblestone and narrow roads makes you feel like you’re in Europe. The weather was cool and dry, so it made for a perfect stroll across Little Italy.


Don’t forget to stop by any of the pastry shops on this side of town. Mike’s Pastry is really popular and can have long waits. Modern Pastry is another option, and they’re open late! That’s where we got these scrumptious cake balls and cannoli below.




Cambridge, M.A. — just a few bus stops away from downtown Boston — is home to Harvard University. If you have a half or full day available, I’d suggest stopping by this part of town to explore more history, and of course, for experience the photo ops!  You can walk through the university or schedule a tour. The historic Harvard Square is full of quaint restaurants, bookstores, gift shops, coffee shops and more.



Seaport District


Ever wanted to dump tea into the Boston Harbor like the colonists did back in the 1700s? Visit the Boston Tea Party museum for the ultimate touristy and historical experience. Or at the least, it’s a great spot to take photos of statues like Sam Adams (pictured above), buy souvenirs and interact with the museum staff in colonial costumes. They are a LOT of fun to talk to.


Our walking adventure in Seaport ended at The Envoy Hotel, an upscale, modern hotel. Even if you’re not a hotel guest, you can enjoy drinks at the Lookout Rooftop + Bar and see panoramic views of the city.


Other places to see in Boston

My list could go on for days, so here are some more attractions to consider seeing while in Boston:

The Paul Revere House – A must-see for history buffs. Explore Paul Revere’s old home, which is located off Freedom Trail, and learn the true story behind his legendary midnight ride.

Acorn Street – For an Instgrammable pic, you need to head to Acorn Street. You’ll be glad you did!

Catch a sports game – Boston is known for several popular sports teams such as the Bruins, the Red Sox and the Celtics. I love hockey (huge Stars fan), and it’d be fun to see another famous rink!

Eat and shop at Eataly – For food shopping fun, check out Eataly, an Italian food hall that includes several restaurants, food and beverage counters (including a cannoli counter!), a bakery, retail items for purchase and a cooking school. This is where food nerds need to be! Eataly is located inside Boston’s famed Prudential Center.


Have you been to Boston and have other recommendations? Leave a comment below! Thanks for stopping by GenPink. :-)

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