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Writer's pictureMaddy Rasberry

The Complete Guide to Boston, Massachusetts (My Favorite City)


Ah...Boston! There's something about Boston's rich history and fantastic views that draws me in. Boston is my all time FAVORITE city. In fact, I first travelled to Boston on a school trip, and loved it so much, I brought my family back the next year for a vacation. This blog explains why I think Boston is wicked cool.


What to do: The first day you arrive in Boston, you MUST walk the Freedom Trail. There's a brick path that leads all throughout the city, marking each historic spot. It's great because you can never get lost, just travel along the brick path. I recommend making this a full day experience, making sure you have plenty of time to really take in the historical landmarks and realize the events that took place that lead to where we are now as America. I would also recommend going off the trail if you see something else interesting like a restaurant or cute shop. Walking along the Freedom Trail gives a general idea of where everything is located in the city.



The Boston Commons is located close to the capital building and is a small park, perfect for morning runs and late night talks.


There were swan boats that people could ride in the pond and musicians around the park showing off their skills.


My family and I did a trolley tour which was another great way to know the city of Boston and understand the layout of it. We learned a lot of history and it was great seeing different areas of Boston I hadn't seen when I went previously.


Along the Freedom Trail, you'll find Quincy market. This is one, big food court full of any type of food you can think of. Surrounding the market is shops galore and street performers. It's a perfect area to grab some lunch and people watch.


Visiting the Boston Public Library was one of my favorite places I visited in Boston. There was something about the library that felt like I was in a museum or a movie of some sort.


In the morning, my family and I ate at the Newsfeed cafe located inside the library. We listened to the newscast they do everyday LIVE!

The library also has beautiful architecture that made me feel like I was in a palace while some areas of it seemed more modern. Surprisingly, it really wasn't that crowded anywhere in the library (maybe because it's so big).


Along the Freedom Trail, you'll run into the State Capitol building which is almost impossible to miss. The capital building is beautiful and has a gold roof so it's easy to spot.



I actually took a tour of the inside of it during my first trip to Boston.


The cementaries in Boston are so unique because you're surrounded by beaituful buildings and skyscrapers and right next door there's a strip of land filled with graves of famous people like Samuel Adams or Mother Goose.


The North End of Boston is where you'll find gorgeous brick buildings, old architecture, and even Paul Revere's House.

The North End is my favorite area of Boston because it's unlike any place I've visited before. It has beautiful brick buildings, culture, unique shops, and some of the best restaurants in the world (just my opinion). I seriously wish I could live in this area of Boston. I have about a billion pictures of the North End and didn't want to post them all but it makes me want to book a flight tomorrow just reminiscing of how amazing it is.


This is so random but we passed a building that had a giant, gold tea pot that actually had steam coming out of it! It was so neat!


I love Bunker Hill and the surrounding neighborhood. It's so historical and it's amazing to think about the relevance of the monument.


Be careful though because climbing up Bunker Hill's monument was VERY difficult for me! Getting to the top was not hard, but coming down was! There are no markers coming down so you never know when it will end. My legs were shaking when I exited for 10 minutes straight because I used muscles I usually never use in my legs. Such a weird feeling and I wasn't the only tourist this happened to.


Towards the end of the Freedom Trail is the USS Constitution which is still running today. My dad was having a blast exploring the entire ship.


A perfect place to visit for shopping is Newberry Street. Not only is it beautiful but it's also full of unique shops and expensive clothing.

If you love sea life make sure you check out the Boston aquarium.


The Boston aquarium has whale watching tours which was my FAVORITE part of my trip! We saw so many whales up close! It was almost like they were putting on a show for us! The aquarium knew each of the whales. They do research on them in their natural habitat such as documenting their swim pattern. Two of the whales names were Spoon and Fan. The aquarium had a great narrator that would explain everything happening and where to look at when they spotted certain sea life.


Another favorite of mine was Acorn Street. I remember seeing so many pictures of the street on Pinterest and instagram and thinking it was so cute. I forced my family to find it with me and it was well worth the long walk. I would love to live in this neighborhood. It's so beautiful and I actually have a framed picture of it in my room because that's how much I love it.


Check out this super cool book store called Brattle Book Store where half of it is outside in an alley way. It's actually a very famous book store and has sold thousands of dollars in unique, one-of-a-kind books.


I also visited the Museum of Science which was honestly a let down. Its farther away from the main area of Boston and was not a very interesting museum. If I had little kids, it would had been a different experience but definitely not an area for adults.


There is another little market called Boston Public Market. It's such a neat place that has a different atmosphere than Quincy Market and reminds me more of an actual farmers market. There were cute, little shops that I could have spend all day browsing around in.


Where to eat: One of my favorite restaurants I ate at was called Atlantic Fish Co. It's a bit pricey BUT WORTH IT! If you're looking for a dinner fit for a king, with the best service and seafood in the Massachusetts area, this is it.


I had their award winning clam chowder one night while my sister tried their lobster. My family and I loved the restaurant so much, we ate here two or three times our entire stay. Who can beat great food, service, and atmosphere. This is my type of seafood restaurant.


Another must eat restaurant is called Reginas Pizza. It's located in the North End of Boston and seemed like a little hole in the wall place. Luckily, we were able to get a spot right away but inside was packed. Reginas ONLY serves pizza. And I know what you're thinking...just pizza? No salads? No chicken wings? But YA'LL...this was the BEST pizza I EVER ate in my ENTIRE life. Like WOW! I'm used to ordering ranch dressing to dip my pizza in but this was definitely not the pizza you would want to spoil with ranch. When we left the restaurant, it was getting closer to dinner time and there was a giant line outside waiting for open seats which just proved to me how great this little hole in the wall place is. It is worth the wait or come around 2-4pm for a better chance of getting in.



Along the way, my sisters and I found a chocolate shop called L.A. Burdick Handmade Chocolate which was shaped like a little cottage on the outside. It was some of the best chocolate we ever had.


Where to stay: My family and I stayed at the Lennox Hotel. This was by far one of the best hotels we ever stayed at. It was classy, sophisticated, and the staff made me feel like I was royalty. Just take a look at the pictures and you'll notice how wonderful our hotel was.


The Lennox is located right across from the Boston Library and close to Newberry Street and the Prudential Center (great shopping areas). It's in a perfect area of Boston.

This little nook was right outside of our hotel.

The Lennox also had many restaurants attached to it like a bar, Irish restaurant, a brunch spot, and a Lindor CHOCOLATE store hehe. Every day when we came back to our hotel, the staff would set chocolates on our bed. Such a nice touch!


I would go back to Boston in an instant. It is my favorite city and an area that I would seriously consider moving to. I miss you Boston!


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