In every city, each neighborhood has its own unique characteristics and Boston is no exception. But finding a spot in a city that speaks to you is what traveling is all about. My favorite thing about any city is it’s history. And in Boston, history is everywhere! Even the homes are historic dating back to the 1600’s. The city has nine historic districts alone with famous American Revolutionaries that have walked the streets. So if your planning your next trip to Boston and need some guidance… keep reading because this post will tell you where to eat, what to see, where to stay and even what I wore.


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What to see

If you find yourself just walking around the city without a plan, odds are you will probably run into something historic and unique. Here is a list of places in the city that are a must see:

  • Beacon Hill and Back Bay Historic Districts: here you’ll find the oldest streets in Boston, Acorn and Chestnut. Where the streets are lined with original cobble stone and historic brick buildings. It’s the perfect shot for any Instagram lover.
  • Commonwealth Avenue: This area is beautiful with large trees and colorful townhouses lining the street. Must be nice to live there 😉 haha.
  • Boston Public Garden & Boston Commons: just a short walk from Commonwealth Avenue, the Boston Public Garden is very tranquil with its abundance of greenery, trails, flowers and even swan boat rides through the lagoon.
  • Paul Revere Mall Park & House: Get a quick history lesson in as you walk through this park and see the historical landmark of Paul Revere riding his horse. “The British are coming! The British are coming!”
  • Rose Fitzgerald Kennedy Greenway Park: while walking around town, I found this charming little play/lounge area for kids and adults which I thought I’d put on this list. My inner child wanted to run, play and splash around the water spouts at this fun park (maybe next time 😉 haha).
  • North End: this little area located towards the Boston Harbor is known for being Boston’s “Little Italy”. On Salem and Hanover Street you’ll find Italian restaurants as far as the eye can see. One right after another!
  • Boston Harbor: No Boston trip is complete without taking a walk along the “Ha-bah” (Harbor) haha. A good place to relax by the water is the Boston Harbor Islands located in the North End.

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Where to Eat

Since I was only in the city for a short weekend I only have a couple places I’d recommend but if I’m being honest… it’s not hard to find a good meal in this charming town.

  • La Famiglia Giorgio’s: be prepared to wait in line, its worth it!
  • Mikes Pastry’s: skip the long line here and go during the evening (I noticed it was dead around the 6 o’clock hour). Grab a cannoli its amazing!
  • Tatte Bakery: this trendy little coffee shop is adorned with white subway tiles, Carrara marble counter tops and urban decor. Perfect for any instagramer and lover of coffee.
  • Saus: I freaked out with excitement when I looked at the menu and it said “Canadian style poutine fries”! (Shoutout to my Canadian friends Aye!) If you know what poutine is, great! If you don’t… YOU NEED TO GO TO Saus and try them. It’s just french fries with cheese curds topped with a gravy sauce. *Also try the Biscoff cookie spread waffle!
  • Boston Burger Company: O.K. hands down the coolest and delicious burger I had in a while here! This place not only has a funny menu with 18+ different yummy burgers (with funny names like “Artery Clogger” haha) but also CRAZY milkshakes! I enjoyed the Whiskey Tango Foxtrot burger with a chocolate peanut butter banana milkshake. YUM! It put me in a food coma for sure. 

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Where to Stay

I stayed at the iconic Boston Park Plaza Hotel and Towers which is located right in the center of the city. Perfect for walking around with out having to drive everywhere and find parking. Although this hotel charges $50 a night for valet parking, its worth it because finding a parking spot in Boston is almost impossible. The building is a national historic landmark that was newly renovated to it’s modern-trendy style that it is today. Not only does this place have historical ruins, it also has an abundance of entertainment. Whether you’re having cocktail hour in the library, breakfast in the grand lobby, or dinner at their signature Off the Common restaurant this hotel will not disappoint. 

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What I Wore

For this particular trip I had Madewell by my side to help me dress for a weekend of sightseeing. Currently, they have an amazing summer sale going on with an extra 15% off sale items! I was so excited because I snagged some cute tops for only $9 and signature jeans for $30. Talk about a major deal!!!

Jeans // similar light striped top // top // similar “Santa Cruz” top // Bandana (neck tie) in twilight // sunglasses // Boat shoes (navy) // Berry Heeled sandals // shorts // cross crossbody bag in red // 



It was a great fun filled weekend in Boston and I hope you find this “guide” useful. I found that with so many unique places in this one small city, no matter who you are you’ll find somewhere in Boston to call home. Can’t wait to visit again!

***Special thanks to Madewell for making this blog post possible! Shop their summer sale now.

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