Boston travel guide

I returned to Boston last spring for my 22nd birthday weekend. Actually, not really on my birthday because a bomb cyclone (basically a coastal snowstorm) hit the city the day of our departure and all flights were cancelled. So I ended up rescheduling the trip in April for a belated birthday weekend with my cousin! I was super disappointed to not go on my actual birthday, but the weather ended up being much nicer in April, and the city was in bloom.

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I’d been to Boston for the first time at the ripe young age of 11 when bermuda shorts were in and racerback tanks made up my entire summer uniform. I was there for my older cousin’s wedding, and it was the last, greatest cousin vacation ever before we all grew up and went separate ways. Three of the families (mine included) rented white minivans and we caravaned our way all over Boston and Cambridge and beyond the week after the wedding. It was fun and memorable for so many reasons.

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I quickly realized after arriving in Boston that traveling with family like that is so different from travel in your 20’s. Financial constraints, changed accommodations, an altered perspective, all the reasons for a city to look and feel different than I remembered. I lived like a queen in my Boston hotel the first time around…double bed all to myself, unlimited breakfast buffet where I’d meet my cousins every morning, hot tubbing after a day of exploring the city, my own bathroom, etc., but this time I opted to stay in a hostel (I was missing Europe and the ease of hostel life) which ended up being not so great. I also chose to return to Boston because I was sorely missing Italy. But was Boston the antidote for this? No, I found out. It just left me longing for Italy more.

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Regardless, visiting Boston still left me feeling excited as only travel can, and I was thankful I made the trip. Reveling in the beauty of Commonwealth Avenue, grabbing gelato in Back Bay, admiring the art at the Isabella Stewart Gardner Museum and the Museum of Fine Arts, eating delicious pasta in the North End, revisiting the JFK Presidential Library (truly a must visit), and judging Boston’s cannoli feud for ourselves all made for a great weekend.

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Does anyone else like to plan travel on their birthday? Let me know in the comments below! I spent my 21st birthday in Verona and Venice, my 22nd in Boston, and sadly was home for my 23rd (after traveling to Europe in January I was low on travel funds) but I want to make it a tradition again…it’s hard not to have a memorable birthday when you’re exploring somewhere away from home.

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I figured it was finally time to for me to get my weekend guide to the city up on the blog! Like my New York Travel Guide, I decided to link to the PDF version. If you’re more of a printed-itinerary kind of girl like me, this should be perfect. I hope this helps you enjoy the best of Boston while you are there! I am trying out different formats for my travel guides, so let me know if you have any thoughts/recommendations in the comments below.

Click the image below to access the guide!