Boston <3

I went to Boston for my senior trip after I graduated from high school, so I knew most of the places that I wanted to see during our most recent trip to Boston. But, it has been about 3 years since I had been there so there were also a lot of things that I had forgotten. So, naturally I started looking up things on Pinterest about Boston trying to figure out some other things that we had do see/do on our trip. But, in my searching I didn’t really find anything that helped. When I travel I like to do and see more of the local culture instead of just doing touristy things, so I was a little disappointed when everything on Pinterest was touristy things. So, because of that, I made it my goal for our most recent trip to figure out some of the best things to do that hit both the local culture and the touristy sites.

So… Here are some of the must see’s and do’s & trips and tricks for Boston, MA. All of this is my own opinion, so take it for what it’s worth. 😉

  1. Fenway Park

I am a huuugggggeeee Red Sox fan (obviously ;P) which is one of the main reasons we chose to go to Boston this year. But, even if you aren’t a baseball fan or a Red Sox fan, going to Fenway Park is probably the biggest MUST to do in Boston. It is one of the most incredible places in the entire world. Red Sox fans are so loyal and love their team, so the atmosphere is so competitive, fun, and amazing. The traditions that go on at each game make it that much more special. The fans have individual cheers for many different players, each time a Red Sox player scores they play a sweet pump up song, they sing ‘Take Me Out To The Ball Game’ for the seventh inning stretch, they passionately sing ‘Sweet Caroline’ in the 8th inning (my favorite part. I seriously cry.), and the songs after the game if they win.. like holy cow. I cannot even put into words how incredible this place is. It truly is almost like a spiritual place. Not even kidding. If you go to Boston, you HAVE to go to Fenway. Plus, what better thing to do on vacation than watch a baseball game, at least in my opinion. 😉

Not only is it such an amazing environment, but the history of Fenway is very fascinating. Fenway Park is the oldest operating baseball stadium, so it’s been through a lot. The stadium itself is not that big, but to listen to the ins and outs of the history and why Fenway is the way it is, is freaking awesome. So, not only should you go to at least one baseball game while you are in Boston, you also have to make sure you go on the Fenway Park tour. I promise you will not be disappointed. The tour guides are the cutest, most entertaining, awesome people who love Fenway and want to share their love for Fenway with you. Also, the cool thing about the tour is that you get to go to so many different places in the stadium that you normally wouldn’t get to go to if you were just going to a game. You see so many awesome angles of the field and let me just say, each angle is breathtakingly beautiful in its own way. Like, seriously, just walking into Fenway for the first time is incredible enough to make a person cry. Best. Place. Ever.

2.  The Freedom Trail

The Freedom Trail is a more popular, touristy thing to do in Boston. It consists of a trail of red bricks throughout the city that stops at many different historical sights. The history is so rich in Boston, and many of the sights that the Freedom Trail stops at are old buildings or old sites that historical events actually happened at such as the Boston Massacre, Bunker Hill, the Boston Tea Party, and many more. The buildings are so old and so beautifully made that is makes the walk so worth it. Plus, being able to see places that brought our country together brings a deep gratitude for our freedoms that we have today. So, definitely make time to follow the Freedom Trail, and WALK it. I personally don’t think you get the full effect if you don’t walk. However, if you can’t or don’t want to walk there are different trolleys and tours that you can take, but they are a little pricey and busy. So, just walk and soak it all in. It’s worth it. 😉

3. Ghost & Gravestones Tour

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So, this is maybe a little weird, but the cemeteries in Boston are seriously beautiful! They are so different and unique and sorta awesome. It’s kind of interesting, too, because you’ll be walking around downtown Boston and all the sudden walk past a random cemetery. Haha Which is fun because the cemeteries also have some crazy history that comes along with their unique beauty.

Fun fact: In the past, they started running out of room to bury people because the city was growing with buildings, so instead of finding a place to make a new cemetery they started burying up to 10 people in the same grave!

The Ghosts & Gravestones Tour is an absolute must to go on. The college students put on a great tour that takes you around some of the ghost history of Boston. You go to many different cemeteries, see where some famous people are buried, and listen to some fun stories. It’s about an hour and a half long, and super awesome. So, make sure you take the time to hit this tour.

4. Little Italy

Little Italy has my heart, like if I lived in Boston this is where I would want to live. Little Italy is located in the North End of Boston. It is very beautiful and very old. It is actually the cities oldest residential area. I’m not exactly sure why I love it so much, I just think you get so much of the Italian/New Englander feel and culture in this area and its incredible. I could walk around Little Italy for hours and hours. If you do go to Little Italy, don’t go in expecting a destination, but expecting to soak in culture and enjoy the walk.

Two musts in Little Italy..

  • Mike’s Pastry: like seriously the most delicious pastries. So, definitely go there and get at least 2 different things per person so you can try lots of things. 😛
  • Regina’s Pizza: okay. There are lots of different Regina’s Pizza all throughout Boston and they are all equally delicious. BUT, if you go to one, you have to go to the one in Little Italy because it is one of the first ones and it just throws you right into the Little Italy culture.

5. Harvard Square

Take the subway and head over to Cambridge to venture around Harvard Square. It is fun to see how the smart people live. lol. This is another thing that isn’t necessarily something you go to to see a certain destination, but more to walk around and soak up the culture and history. However, one thing you must do is stop by and rub John Harvard’s foot for some good luck. 😉

6. Prudential Tower (Top of the Hub Restaurant)

Eating at Top of The Hub Restaurant in the Prudential Tower is so awesome. It is a pretty dang nice restaurant on the 52nd floor of one of the tallest buildings in Boston. The restaurant has windows so you can look out at every single angle of Boston and see for miles. Plus, they love tourists so feel free going in your touristy attire!

7. Salem, MA

Unfortunately, this most recent trip we weren’t able to do any sort of ferry ride because of the weather. If the weather is good, I would definitely suggest taking a ferry ride over to Salem. Any ferry ride would be cool, I’m sure, but we did the one to Salem when we went for my senior trip and I was very impressed with the views AND the nap I got on the ferry. Haha! Jk. I do remember taking a little nap on the ferry, but once we got to Salem I was wide awake and ready to learn about some witches. I loved learning about the Salem Witch Trials in high school so to actually be in Salem and learn more about the history was freaking sweet! If you aren’t into that sort of thing, then maybe take a different ferry. But, I would definitely recommend at least a couple hours spent in Salem.

8. Cheer’s

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I have never actually seen the old show about Cheers. But, I will say that it is still worth stopping by and getting a picture at. There is also a cool little museum to walk through that I thought was super awesome. I love little random history and fun facts so I think things like this are super duper cool to see in person.

9. Boston Commons

Boston Commons is a really cool place because its the commons. lol. But, seriously, there are lots of cool things that go on here. Boston Commons is a starting point to the Freedom Trail, people come just hang out here, walk their dogs, run, and sometimes even do some crazy, random things. It’s fun to just sit and people watch here. It’s also an extremely beautiful place- a beautiful park with a beautiful city surrounding it. Make sure you walk around the Boston Commons and see the Frog Pond, the Public Garden area, and the cute little ducklings. There are always cute little ducklings and swans!

Fun Fact: there was a little kids book made about the ducklings in Boston Commons.


You guys, I know that your legs might get a little tired but walk! Walk everywhere. Seriously. It will be worth it! The first day we were there during this trip we walked 30,000 steps and then the other days we walked at least 18,000 steps. Not only do you get to see and feel and experience so much more if you walk, but you’ll just feel so dang good about it. My Fitbit was so happy with me that day. ;P Just trust me, walking is the best way to fully experience Boston.

11. If you don’t walk, take the Subway!

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If you feel like you need to go farther than what is worth walking (like to Harvard Square or something) then take the subway! It can be a little intimidating at first if you haven’t ever been on a subway or used the subway system, but once you get it figured out it is way easier, faster, and cheaper than Uber or taxi.

12. Boston Marathon Finish Line & Bombing Memorial

I would recommend watching the movie ‘Patriots Day’ before you go to Boston. The movie is about the Boston Marathon Bombing and it seriously is one of the best movies ever. I love it. But, not only is it a good movie, it brings a whole different feel walking down Boylston Street knowing more details and gaining more respect for those who were involved in the bombing. There isn’t a memorial built yet, but the city is in the process of building a memorial to put in front of the Marathon Place store on Boylston where the first bomb was located. However, right now there is a tree in front of the store that acts as a memorial. This was a really cool thing to see on this trip. I already loved Boston, but I gained so much more respect for all the people in Boston because of how they came together after such a tragedy. It definitely is a special place, but it is also such an encouraging place as well! This is definitely a must see to show respect, as well as motivate and feel the unity.

13. Walk around the back neighborhoods

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Seriously though, go on the back roads. Go on the main roads. Walk through the businesses. Walk through the neighborhoods. Walk on any and every street that you can and soak it all in. The back roads and neighborhoods are some of my favorites. I love the beauty of the old buildings. I think they have the cutest little houses. I love to see people doing every day life and feeling that I am apart of that by walking past.

When I went with my parents for my senior trip, we walked down one back road neighborhood one night and ate the most delicious ice cream and listened to some street music and it was seriously one of the top coolest experiences in my life. I don’t know how often people are out playing music in the streets of the neighborhoods, but if you happen to come across this, stop and enjoy it. It was seriously like in the movies. It was definitely one of those nights where you wish time would just stop. Ahh… it gives me have butterflies just thinking about it.

14. Must Eat’s

  • Cask’n Flagon is right by Fenway Park. It is the oldest restaurant still running next to Fenway and is absolutely delicious. Sounds a little gross, but the baked macaroni and cheese is pretty dang good! It’s always packed and is definitely worth the wait.
  • Dillon’s is right by this cute firehouse so I had to throw the cute firehouse picture in here too. (Fun Fact: this is a super old fire house and actually caught on fire, but it is still in operation today) Anyway, Dillon’s is pretty dang good. If you see the firehouse then you know you’re at Dillon’s. Get the sliders at Dillon’s. Mmmhhmm.. they are delicious.
  • Terry C’s Bar and Grill is also close to Fenway and was really really tasty. I got a delicious, juicy burger there.

I would definitely say eat at as many places as you possibly can because the food is soooo good! Of course you have to get some lobster and clam chowder while you are there. When I went with my parents we seriously ate at least 2 dinners a night just to try different places. LOL. It was so worth it!

15. Go With People You Love

I mean, this is kind of a no brainer, but go with people you love. Both times I went to Boston I was with some of my very favorite people. Experiencing Boston is great and amazing, but experiencing it with people you love and who are passionate about the same things you are is unreal! It is an unforgettable trip to say the least. I love these people so much and am so grateful I got to experience these trips with them.


I am already counting down the days until our next trip to Boston. ❤





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