15 Best Things To Do In Boston – A Travel Recap

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The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

If you follow my Insta-stories, then you most certainly saw that Jessica and myself took a trip to Boston a couple weeks back. This was her first trip up to Beantown, and I hadn’t been in about eight years. It was exciting to see everything and play tourist in such a historic city. So why did we head up to Massachusetts in the first place? Well,  big news for anyone who lives in Atlanta – JetBlue is here! Well, sort of. They’ve finally added a Boston (their hub) to ATL route! We were excited to partner with them to share the big news and enjoyed a complimentary roundtrip flight (and Even More Space seats) to get to Boston.

Once we arrived in Boston though, we wanted to make sure we were hitting all the hot spots that tourists need to check out when visiting the city. Specifically where to stay, what to do, and where to eat. A big THANK YOU to the Boston Tourism Board and the Cambridge Tourism Board for setting us up with the most amazing itinerary. From our hotel accommodations to attraction passes and meals – we were set!

So today, I’m excited to share a full recap of the 15 best things to do in Boston, which is basically everything we did, hahaha! No surprise here, the majority of my highlights include food. Y’all know the best part of any trip are all the local meals and cuisine you get to try. Plus it was SO rainy and cold while we were there, so taking cover inside was essential to our survival against the elements. So here we go, hope this post inspires you to make your own trip to Boston soon, enjoy!

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

WHERE TO STAY

The few times I had visited Boston before, I stayed with a girlfriend who lived outside of the city. So I had no idea where to stay when it came to finding a hotel. Thankfully, we were set up with a suite at The Colonnade Hotel in Boston’s Back Bay.

So for that, my NUMBER ONE thing to do when heading to Boston is to stay at The Colonnade Hotel. Talk about the most perfect home away from home. With floor to ceiling windows, cozy beds, and amazing amenities, this hotel went above and beyond. Plus, did y’all know they’re the only hotel with a rooftop pool in all of Boston! Pretty cool huh? I’ll talk more about that later. But y’all, their staff was so welcoming (just look at that meat and cheese plate we were greeted with!) and helpful with plenty of maps/directions as we made our way around the city.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

WHAT TO DO

As soon as we landed in Boston Wednesday afternoon, we hit the ground running. A quick outfit change and we walked the few blocks over to the Prudential Center where 50-stories up we enjoyed The SkyWalk TourNUMBER TWO on my list! Grab an audio handset and enjoy the 360-degree views of Boston and learn a little bit about everything you see! We enjoyed the SkyWalk before the rain and clouds came through, which is why this is the only picture you’ll see in this entire post with blue skies.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

On our first full day in Boston, the rain was coming down…bad! We had to run into the little shopping center and buy umbrellas and I bought a hoodie I was so cold. Lucky for us, our next adventure on the itinerary at least gave us some shelter. NUMBER THREE on my “Best Of Boston” list – the Duck Tour. This is seriously such a fun way to learn the history of the city and scream “Quack!” a million times. Sorry, no photos y’all. Again, rain. The plastic little sheets were pulled down so we didn’t get soaked so I couldn’t snap any pictures. But our tour guide was hilarious and splashing into the Charles River is always a good time!

Ok, gotta be honest, we didn’t actually get to do NUMBER FOUR on my list. Why? You guessed it. RAIN! The Freedom Trail is something you always hear locals and tourists talk about as a highlight to any Boston outing. Too bad for us, it was about 50 degrees outside, pouring, and a two-mile walk through that just didn’t work out for us. We. Were. FREEZING! And fearful of getting sick. So while we didn’t get to do this tour, I wanted to add it to the list here because I hear it’s amazing and we saw some people taking the tour and were so jealous. This is definitely on the top of my To-Do list for my next Boston trip. Which hopefully will be on a gorgeous spring day full of sunshine! LOL!

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

Right down the street from our hotel was NUMBER FIVE on my list: The Boston Public Library. Y’all, I felt like Belle from Beauty and the Beast! There were books as far as the eye could see (over 6 million) and it was so magical. So glad we snuck in here to get dry from the rain because it was seriously so stunning. The photo here from one of the reading rooms doesn’t even do justice to how large and spectacular it was in person.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

NUMBER SIX has to be the Boston Public Garden. Y’all, can we talk about the vibrant greenery and purple flowers…they were EVERYWHERE! We braved the weather and wanted to see some of the city and so glad we took a detour through the Garden. Jessica and I traded off holding each others umbrella so we could snap some photos. You can see the raindrops in this picture but I still love it. On a better day, I could have spent hours walking through here.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

Not going to lie I had never heard of NUMBER SEVEN on my list – Acorn Street. Jessica said she spotted it as a top tourist spot on Instagram and since we were already in Beacon Hill, we decided to pop over. Y’all, this street is like stepping back in time. 400 years to be exact. Lined with some of the oldest homes in Boston, this cobblestone street was NOT easy to walk up and down. Acorn street is steep and small, and when you add in rain – very slippery! I almost fell a hundred times to get this shot because ya know, #bloggerlife.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

NUMBER EIGHT – The Harvard Tour! Or wait, let me correct myself.  It’s actually called (officially) The Hahvahd Tour. Hands down, one of my favorite part of our whole trip! Our tour guide has graduated the day before (how funny we visited Cambridge/Boston the same week as graduation!) She was funny, personable and had so much insight on the campus. So cool to see the hall where Mark Zuckerberg started Facebook. And I’m pretty sure she said this is the hall where Natalie Portman lived. The entire campus is red bricks and greenery and has a ton of history. Seriously, don’t miss the trip across the river to do this tour it is totally worth it!

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

WHERE TO EAT/DRINK

After we enjoyed The SkyWalk tour I previously mentioned, we went up to the 52nd floor to enjoy dinner at Top of the Hub. Talk about delicious! This restaurant makes NUMBER NINE on my list because y’all, just look at that watermelon and lobster salad – YUM! This is also fun for me because this was my first time ordering a steamed lobster. Like, just a lobster. (Sorry,  no photo, we devoured it.)  It took over the entire plate and was, duh, amazing! Such a great way to kick off our food tour if you will of Boston.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

Who doesn’t love a little pre-dinner cocktail? After our first full day in Boston, we went over to The Ritz-Carlton for a drink. Their Avery Bar, NUMBER 10 on my list, is a cozy spot off the main lobby perfect for grabbing a cocktail and just relaxing. The atmosphere is dark and moody (in a good way) and we kicked up our feet right next to their fireplace. Their wine list and signature cocktails are not to be missed. Plus, make sure you get the little trail mix they leave on your table. The honey glazed pretzels were so addictive we asked for seconds!

After The Avery Bar, we went to my NUMBER 11 spot – Post 390 – for dinner. This urban tavern was a food lovers paradise. We ordered the seafood tower (just for the two of us, ha!) and a salad and split dessert. But let’s talk about this salad we enjoyed for a moment. It was a house made burrata with spring peas, strawberries and asparagus topped off with fried sourdough bread. Y’all. SO GOOD! The waiter said it was brand new and hadn’t even been added to the menu yet. I think this may have been the best thing we ate all trip. (photo c/o Post 390)

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

Whenever anyone asks what I miss most about living in Washington, DC, my answer is always this: sweetgreen and Cava. Seriously. If you’ve been to either then you understand. I miss being able to create my own bowl of deliciousness that’s also healthy. Thank goodness Jessica sent out a request on Twitter asking for a lunch spot recommendation once we arrived in Boston because we were introduced to my new obsession – DIG INN. NUMBER 12 was unassuming on the outside, but when you go in, you can create the most delicious veggie bowls filled with goodies, pretty sure I licked mine clean. In fact, we loved it SO much we went back for breakfast the next day where I enjoyed their overnight oatmeal. I mean, in a 3-day trip if you go to the same food place twice, you know it’s legit! (photo from Dig Inn Instagram by @christianharder)

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

NUMBER 13 is actually a two-for-one meal extravaganza. First, you have to head to Cambridge and go to the Kimpton Marlowe Hotel. Then head to their newly re-designed brandy bar when you walk in. Say hi to Dennis, the master bartender and “brandy man” as I call him. He hosted us for a mini little tasting at the bar where we sipped brandy (who knew I even liked it!) and made us cocktails with his favorite picks. Then, walk a few feet over to Bambara (it’s inside the hotel too) to enjoy one seriously amazing meal. Jessica and I did a little tasting where we chowed down everything on freshly made pasta, octopus, salads, delicious bread, seafood, desserts – the list goes on and on. You can’t order wrong. It was such an amazing experience from start to finish and one I’ll be sure to check out again on my next trip.

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

Oh, the famous Tatte Bakery. This was probably the most mentioned place to go whenever I told y’all I was heading to Boston. And it did NOT disappoint! NUMBER 14 has to go to the iconic Tatte Bakery. This Insta-famous shop (for good reason) was everything we had hoped for and more. We ordered salads, pastries, and coffees and everything was delicious. We stayed here for a long time, to avoid the rain, but also because the food was so good we just kept ordering. There are a handful of locations across Boston and Cambridge, but even if you never make the trip at least just follow them on Instagram. It’s the prettiest, yummiest feed you’ll ever see!

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

And finally, NUMBER 15 on my “Best of Boston” List. I told y’all the Colonnade Hotel ruled right? We happened to be in town for the weekend their iconic rooftop pool (RTP) opened and were hosted for a delicious send-off breakfast poolside before we left for the airport. The sun had finally come out (a little) and the views and ambiance were the perfect way to start the day. Heck, there were even guests swimming! I ordered the blueberry pancakes which were so gigantic and buttery…yum yum yum!

The 15 Best Things To Do In Boston - Travel Guide - Poor Little It Girl

Well, that’s it! Hope this post inspires you to travel to Boston this summer, or at least give you some ideas on what to do, where to stay, and what to eat while up in Beantown. If you like these kinds of travel posts, let me know! I’ve got a few more trips coming up this year and would be happy to share more recaps like this with y’all. Just let me know in the comments below. And of course, check out more of my travel content from my PLIG adventures here!

A BIG thank you to JetBlue, Boston USA and Cambridge USA for taking care of us during this trip and providing us with flights, tickets to the tours and complimentary meals. All views expressed are my own.

A FEW THINGS TO PACK FOR YOUR OWN TRIP TO BOSTON:

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12 Comments

  1. Jill Rymarz

    I’m going to Boston for the first time next week and really enjoyed reading about your trip! Thanks for a putting together this great travel guide!

    Reply