Boston City Guide
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February 5, 2020
I finally made it to New England! Like I mentioned before, it has been my dream for a while to see the area where our nation was founded, and as a city girl, you know I was heading to Boston first. I really lucked out with this trip because Ryan used to live in Boston, so I had a knowledgable tour guide the entire time. Boston is actually a pretty small city, and it’s super easy to explore in just a few days. Ryan and I had two days there and while we weren’t able to do everything we wanted (I like to sleep in, oops), we did get to do a lot. Here’s my Boston city guide for all the areas we went to in the city!
Cambridge
The first area we explored in the Boston area was Cambridge. It was adorable. Cambridge is so peaceful and pretty in most areas, but very lively and vibrant along the main stretch, Cambridge Square. Cambridge is just across the river from Boston and is the home to Harvard University. It’s incredibly charming, beautiful, and quite quaint. I could totally see myself living here if I were to ever live in Boston.
Back Bay
Back Bay was our number one choice for where to stay in Boston and we did so, right in the middle of Copley Square. This area of town is very active during the day with lots of businesses, restaurants, and shops. There was this one little pub called Solas that we kept going back to. If I lived in this area, it would totally be my little neighbrohood go-to! If you go, get the pretzel bites. They’re phenomenal! It was definitely my favorite area we shopped in. Newbury Street has tons of great shops – I could have spent the entire day here! But, of course, there was too much to see.
The North End
I absolutely loved The North End, though I am still glad we stayed in Back Bay. It’s a very cool area that kind of reminds me of the best parts of Brookyln. It’s lively, but intimate at the same time. There are tons of restaurants, especially Italian restaurants as that is what the area is known for. We opted for pizza (you know how I dzo), and oh my god. It was amazing. Definitely some of the best pizza I’ve ever had, and I’ve had a lot. The place we went was called Regina Pizzeria. It’s famous for a reason, yall.
Seaport
Seaport was where literally every single person told us to go. Apparently it has changed a ton in the past few years and according to one Uber driver, it “looks like Dubai.” I wouldn’t take it that far, but it was a really cool area to see. There are lots of tall buildings, but just as many smaller ground-level restaurants and shops. My favorite thing we did in Seaport was go to a couple different breweries. Harpoon was awesome – we loved the beer and pretzels! And Trillium had a really cool vibe, but could have had better beer.
Downtown Crossing
I actually really liked downtown and I might stay in this area next time. I love walkable areas, and downtown certainly is. It’s right by the Boston Public Garden, which is very pretty and calming for a park in the middle of a city. Downtown is actually a lot cleaner than I’d expect any downtown area to be and lots of the walkable area does not allow cars, which is great for exploring on foot!
The South End
This area of Boston is known for its intimate, very highly rated, reservations-only restaurants. Unfortunately, we didn’t have time to make it down to the South End, but I had to mention it in the guide because it’s the top thing we missed that we really wanted to do!
Overall it was such a great trip and I would totally go back!
Pin for Later:
What would you add to my Boston city guide?
Photos by Ryan Carpenter.
October 26, 2019 @ 8:28 am
Sofun! I’ve only been to Boston once but I’ve been all over the surrounding towns! I would definitely like to go again! Yay for all the PIZZA too!
October 28, 2019 @ 4:37 pm
Omg the pizza was SO GOOD!! It’s such a fun city!
October 27, 2019 @ 7:35 pm
Great post! I like the idea of exploring downtown. Unfortunately, they are cities were downtown is not walkable and is not safe. I’d love to visit the Boston Public Garden!
October 28, 2019 @ 4:37 pm
That’s true! Walking around is my favorite. I love to explore and just stumble upon locals bars and restaurants along the way!
October 27, 2019 @ 8:16 pm
my husband is from boston! it’s one of my favorite cities. there is so much history! these photos are beautiful btw!
October 28, 2019 @ 4:36 pm
Oh no way! How cool! Yes, sooo much history. I want to go back and do some more exploring!
October 27, 2019 @ 10:59 pm
Ah! Those boots are so lovely. And Boston is a great place – I need to head back up there. New England is a fab area!!
October 28, 2019 @ 4:35 pm
Aren’t they fab!? I’m so in love!! It really was so cute up there. Too cold for me during the winters though, that’s for sure!
October 30, 2019 @ 9:21 am
I need to visit Boston more. I went 2 years ago in the winter but would love to go during the Fall. Love this guide.
October 30, 2019 @ 11:08 am
I definitely want to go back too! I wish we would’ve seen a little more foliage so I’ll just have go back again 😉
November 1, 2019 @ 6:13 am
This came right on time as Boston is next on my travel list! I’ve heard great things about Back Bay and Seaport! Definitely using this guide as a reference!
November 3, 2019 @ 9:18 pm
Oh perfect!! Back Bay was definitely amazing. Have so much fun!
January 11, 2022 @ 7:27 am
I love Boston! The best city I’ve ever been to. I am glad to return there again and again.
January 12, 2022 @ 7:14 am
It’s a really cool city! I’d love to go back and do a little more exploring 🙂