Eats,  North America,  USA

unexpected stops and styles: boston

Travel, if anything, has taught me that there are multiple parts of me with totally different styles.

Seriously- I can dress like a dirty hippie one day, grunge the next, and like a total prep the day after.

Boston is a city that totally gets that! There are plenty of little burrows of Boston that have their own individual styles and personalities, and even better? You can access the majority of them via MBTA.

Here are my favorite neighborhoods within the Boston area.

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If you’re feeling grunge/alternative…

Head over to Central Square! This little area has plenty of restaurants, thrift shops, and street art.

Don’t Miss:

Graffiti Alley: a small, ever-changing, easily missed alley absolutely covered in graffiti. Over the weekend, I was there twice in one day, and there was art added while I was gone!

Cheapo Records: Cheapo records is the kind of place you want to go into and just browse. Pick up an oldie (but goodie) record or cassette, or buy a random one and give it a listen!

Toscanini’s: Yeah, they’ve got the classic ice cream flavors (which are delicious), but the best flavors (in my humble opinion!) are the unique ones. Try B3 (brown sugar, brown butter, brownies) and the malted vanilla!

Nearest T Stop: Central, red line


If you’re feeling chic…

Newbury Street is your place! Shi-shi stores and cafes line the entire span of the street. Newbury Street is in a beautiful area, and the end of the shopping street is greeted with Boston Commons.

Don’t Miss:

Sonsie:  The set up is quite like a small European Cafe- perfect for people watching! Try the fall drinks- the caramel apple latte was a hit!

Georgetown Cupcakes: A chain of the bakery that the show DC Cupcakes was based on. Absolutely delicious, a must-have for every trip to Newbury Street!

Nearest T Stop: Park Street, green and red lines

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note: this photo does not capture preppy vibes

If you’re feeling preppy…

Put on your boat shoes and take a walk along Long Wharf! Long Wharf is a little area not so much defined by restaurants and cafes, but more so the water that surrounds it. It’s possibly my favorite area in Boston.

Don’t Miss:

Christopher Columbus Park: Home of Shakespeare in the Park and a beautiful little picnic place, Columbus Park is a great place to walk through or stop at. Even more magical at night.

Nearest T Stop: Aquarium, blue line


If you’re feeling European-inspired…


North End is the place to go! The “Little Italy” of Boston is the best place to stop by for a bite of Italy.

Don’t Miss:

Regina Pizzeria: Ok, so this is a chain restaurant, but the one in North End is the original spot & simply charming (oh and their pizza is really good). Sit in and have a slice (or whole pizza), or take it home!

Mike’s Pastries: Hands down, THE best cannoli I have ever had. Strongly recommend. 10/10. Super flaky shells and the richest filling you’ll ever have. SoooOOOOoooo good.

Nearest T Stop: Haymarket, Green & Orange lines

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If you’re feeling like a mix of styles…

Harvard Square is your place! Harvard Square, like Harvard University, is a very big mix of all different kinds of people and style. Definitely take a stroll around here- it’s a great little place.

Don’t Miss:

LA Burdick: Hands down, the best hot chocolate I’ve ever had. Choose from dark hot chocolate, white hot chocolate, or milk hot chocolate, or tea/coffee! Take it to go and sit in the middle of…
Radcliffe & Harvard Yard: Great to walk through and great to sit down in if the weather’s nice! Harvard Yard is beautiful and lively, and Radcliffe Yard is a little quieter, but just as beautiful!

Nearest T Stop: Harvard, red line

Of course, there are many other bits of Boston worth checking out, but these are my favorites!


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