Boston Itinerary – A Weekend Getaway


I took a quick trip to Boston for a convention and was able to sneak away from meetings a few times to explore what the city has to offer. If you’re planning a trip to Boston soon consider these spots for your itinerary:

  • As the USA’s oldest public park, Boston Common, is great place to begin exploring the city. It is the Central Park of Boston and home to one of Boston’s oldest graveyards, several historic monuments and (as of four years ago) a carousel.fullsizeoutput_6c6e
    • The Freedom Trail is a 2.5 mile route that passes through 16 historically significant sites, with one of the starting points in the Boston Common. I must admit, I am not too big on history so I did not prioritize the trail and only saw the monuments near the park.fullsizeoutput_6c6a.jpeg
    • My friend and I also came across a Shakespeare on the Common, a fully staged Shakespeare production that is free of charge and has been a Boston tradition since 1966.  It was my first Shakespeare in the Park experience and I loved how the actors interacted with the crowd members to keep them engaged. You can choose to either lay out on a blanket or rent one of the beach chairs located front and center. (Warning: there is a 75% chance laying on the grass will lead to a nap, that was 100% for me 😅)IMG_2311
    • If you kept up with my Instagram story during my trip you know how yum Daddy’s Fried Dough was, unfortunately, my phone died right when I ordered so I did not get any good pictures to justify this claim so please take my word for it and give it a try. I disregarded the menu and asked him for the best one he’s ever made, it looked so good that a baker came up to us at the park and asked us what we were eating so she could get herself one too. This is located at the entrance of the Boston Commons that is right across the street from the Public Garden entrance.

      The last picture I took before my phone died
  • As one of the USA’s first botanical garden The Pubic Garden set quite a precedent for others to follow – there’s also a white squirrel constantly stealing the flowers attention fullsizeoutput_6c89



  • Fenway Park is the oldest MLB stadium – if you haven’t realized yet Boston is all about being the first and oldest. If your trip is planned during the baseball season I recommend trying to experience a game at the stadium. (P.S. contrary to what these pictures may demonstrate I am still a loyal Yankee fan)



  • Newbury Street now a heavy tourist and retail destination was once a prestigious and exclusive residential area. Although the ambiance of the neighborhood has changed the 19th Century European influenced architecture remains intact. fullsizeoutput_6c75fullsizeoutput_6ca7
  • Referred to as New England’s best view, the Prudential Skywalk Observatory, is the only place to catch a sky-high 360° view of the greater Boston area. I love observatories because you can get a sense of the size, history and development of an area in a short amount of time. Observatories have the ability to make you feel so small, so quickly; I always reflect on where I’ve been, what I’ve done and how it impacts the grander scheme of things as I’m reminded even in the smallest cities that the world is such a big place.
    One of the few skyscrapers stands out like a sore thumb
    In the distance you can see Fenway park, much closer you see the Boston traffic
    Red bricks fill The Greater Boston Area

    There are various facts about the history and people of Boston along the walls of the observatory
  • First off I must say finding good, homemade ice cream in Boston was a bit more difficult than I anticipated. My friends and I traveled to Cambridge to try Honeycomb Creamery, a woman owned local ice cream shop with unique flavors that are made totally from scratch and locally sourced. The batches of ice cream are small so the flavors are constantly changing and as you can see from the menu these flavors really get you out of your comfort zone so be open-minded and give them a try! IMG_2653


  • I was not able to do the Boston Duck Tour but I’ve heard phenomenal things about it, it gives you a full tour of the Greater Boston area on both land and sea fullsizeoutput_6c6d

I hope the places I visited while in Boston help you build out your itinerary! If you have any questions or any suggestions of places to see during my next visit make sure to comment or message me!

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