I was born and raised in New York. Grand Central Terminal brings with it overwhelming nostalgia and anxiety alike. I was raised on cawfee, eggandcheeses & pizza. I don’t even know what it would feel like to not be a Yankee fan. So naturally, I have avoided Boston at all costs. I’d always imagined it to be this faraway land full of angry Red Sox fans eating those gross doughnuts filled with oozing cream. But lately I’ve decided I really want to see the world and that includes the very country I live in. So this month my boyfriend and I set off for a mini vacation in Boston. Much to our surprise, we had the best time of our lives and enjoyed every last second. If you’re going to be in Boston for 3 days and have no idea where to start here’s the way to do it:

Day 1:

We left New York at 6 am which gave us enough time to have 4 pee breaks and arrive in Boston at 10 am.. just in time for breakfast!

The Friendly Toast – 35 Stanhope Street (Back Bay)

Tip: If you don’t get an order of home fries, get TWO orders like we did!

Next we drove to Cambridge. I know it isn’t technically Boston, but we think your trip wouldn’t be complete without this part. Plus, we had some time to kill before it was time to check into our Airbnb. (PS- It was our first time staying in one and we loved it!)

Harvard Square– 18 Brattle Street (Cambridge)

Harvard has a gorgeous campus and it’s fun walking around pretending to be a student or maybe a future parent visiting your genius kids! With all this walking you’re going to work up an appetite and have to stop for snacks for sure! I know we did!

Insomnia Cookies– 65 Mt. Auburn Street (Cambridge)

These weren’t around when I went to college but they seem to be a staple at every college campus nowadays. I mean, I can see why! Cookie delivery while studying for finals? I think yes!

After this we headed towards MIT. Since we still had the car we drove, but looking back I would recommend walking because there are tons of things to see on the way like Modica Way, an alley way dedicated to graffiti & street art, which is totally up our alley!! (Pun intended) Finish it off with a drive or walk over the Harvard Bridge and take in all the views.

Around 2 PM we drove back to Boston’s Back Bay area to check into our Airbnb, which was the perfect location for our stay and I’d definitely recommend it. It’s walking distance to almost all the sites we wanted to see and if you feel comfortable taking the T (Boston lingo for the train- yes, I know I’m so cool) it was about a block away from the Back Bay station. The neighborhood has such a Brooklyn vibe and we stayed in the most adorable apartment.

 

After settling in, we decided to take a walk in our neighborhood. We were walking distance from the finish line of the Boston Marathon and since my BF is a NYC-marathoner, it was a must-see on our list! I didn’t complain because there was a great Irish Pub right next to it where I got to have my first Sam Adams of the trip! There was actually a guy from Dublin there, so you know it had to be good!

Solas Irish Pub– 710 Boylston Street (Back Bay)

 

 

For dinner we decided to keep with the Cambridge theme of the day and go to a place that was recommended to us by a family member. Food is my favorite part of any day & dinner is my favorite meal so my poor decision-making skills really get a workout in this department. So glad we made the absolute BEST choice!

Giulia– 1682 Massachusetts Avenue (Cambridge)

 

This place honestly might be on my list of Top 5 places I have ever been in my life! Every dish left us wanting more but also perfectly satisfied at the same time. YUM!!

Tip: Make a reservation a day ahead if you want to get a table. Even on a Monday night this place was completely booked. We sat at the bar, which turned out to be great because the bartenders were 2 of the nicest guys we’d ever met. They were full of great suggestions of places to go too! But to be honest, I would have sat on the roof for this food!

Day 2:

Let me just say, I’m REALLY not a breakfast person. (Yea, yea, I know, most important meal of the day *rolls eyes*) But breakfast in Boston had me turning into a morning person!

Flour Bakery + Cafe- 131 Clarendon Street (Back Bay)

 

This sandwich was so delicious I wrapped up half and took it home with me! (Just saying) From here we walked to Boston’s North End & took a walk along Harborwalk. My favorite part was that it wasn’t crowded at all so we were able to enjoy the views and feel  like we had the place to ourselves.

 

The North End is home to Boston’s Little Italy. It’s much smaller than NY’s but gives you that same feeling as soon as you walk through. And by feeling I mean, the indescribable NEED to walk into a pastry shop and devour some cannolis and espresso, which brought us to our next stop.

Mike’s Pastry– 300 Hanover Street (Little Italy)

 

Tip: Look like a local and just walk up to the counter & tell them your order even if it looks like there’s a line & bring cash! If you feel like eating your cannoli outside walk over to the Rose Kennedy Greenway and swing on one of their porch swings in their North End Park. People watching and eating pastries at the same damn time!

Next we decided to do a little shopping… in a food market that is! Have you caught on that we love food more than anything?

Boston Public Market– 100 Hanover Street

So many awesome vendors in this place! If you want to get a really unique piece for your home check out American Stonecraft. We bought a cook slab as a gift & it was a hit!

Our next stop might have been my favorite of the whole trip. Although I hardly ever get to sit down and read anymore, I am and always will be a book lover.

Brattle Book Shop– 9 West Street (Downtown)

 

This place, one of America’s oldest and largest used book shops, really is a book lover’s dream. As soon as you walk near the place you get that sweet smell of pages and pages of information and imaginations. Browse through the outside sale lot and find gems for as little as $1. There’s just something about reading through books that have been bent and highlighted and marked up by readers before you. Not to mention, they are housed between 2 gorgeous brick walls beneath all the neighborhood fire escapes. Pure magic!

Chinatown was our next stop and boy, were we ready to have some of the best dim sum in town!

Windsor Dim Sum Cafe– 10 Tyler Street

 

 

This tiny spot was tucked away up a narrow flight of stairs. From the look of it probably not a place we would have gone in, but it comes up on every list of the best dim sum spots in Boston’s Chinatown and now we know why! All the dumplings are made fresh to order and they have over 40 options to choose from! We decided on some classics and some more unique ones like these fried shrimp balls that were amazing!

Afterwards, we walked over to one of the most talked about landmarks in Boston.

Boston Public Garden– 4 Charles Street 

 

Here we got to see a real family of swans protecting their nest & of course we took a ride on one of the swan boats! After all, we were tourists in this beautiful city. Plus, $4 for a nice relaxing sail around the park… sign us up! Not only is the park beautiful, but it’s full of fun facts & history. It was the first public botanical garden in America! It’s also been the location for the filming of some of our favorite movies! Guess what classic this bench is from! (we went twice just to get the perfect shot)

 

*Hint* Matt Damon & Robin Williams sat in this very spot to have a convo!

If you’re up for more walking, take a stroll around Beacon Hill and imagine you live in one of the gorgeous houses in the area. These neighborhoods are dream worthy.

 

When you’ve had enough daydreaming, head over to the home of the Boston Red Sox and have a drink in the awesome bar that’s right on the field.

Fenway Park– 4 Yawkey Way

Bleacher Bar– 82A Landsowne Street 

 

Of course we would take a pic of the Babe! (Yankee fans always & forever)

For dinner I really wanted some seafood in a restaurant with a Boston vibe. We headed back towards the Seaport District where we started the day and took in the views of the harbor at sunset before lobster time!!

 

The Barking Crab– 88 Sleeper Street (Seaport District)

 

What’s a trip to Boston without some New England clam chowder and a lobster roll? Needless to say these were both delicious and the place had a nice, chill vibe. We ended the day with a ride on the T back home and a walk in our neighborhood.

Honestly, could our street BE any cuter? (Chandler Street) & if you didn’t get my Friends pun, well, you need to watch more Friends…

Day 3

By this time, we were morphing into Red Sox fans and contemplating the best way to move into our Airbnb. We really didn’t want to leave & honestly these breakfast options all at walking distance weren’t making it any easier!

South End Buttery– 314 Shawmut Avenue 

 

Tip: Order the buttery biscuit sandwich and the salted caramel mocha. It was the best. Although I might be biased.. it’s all I had and all I ever want to have again! The smell alone from these biscuits is enough to make you drool.

We decided to walk off the breakfast calories by taking our last walk around South End and stumbled upon the biggest community garden we had ever seen. If gardens are your thing, this is a must-see! Got me wondering how we could make something like this happen in our community!

Berkeley Community Garden– East Berkeley Street (South End)

 

Next we headed over to do some of Boston’s most touristy things.

Faneuil Hall/ Quincy Market– 4 S Market Street

 

Here you can shop for just about anything and everything. There are well-known stores in their mall area. Or you can pick up some souvenirs at one of the many kiosks. There are also restaurants and other small shops along the way. After shopping we made a pit stop and had a drink with a friend.

Bostonia Public House– 131 State Street

They are known for their elaborate bloody mary drinks but I opted for the Rose All Day… and let’s just say I was feeling its effects pretty much all day, which made it a lot of fun!

As you can probably tell we are fans of seeing iconic things from movies and TV shows in real life so our next stop was on our must-see list.

Cheers Beacon Hill– 84 Beacon Street

Originally named the Bull & Finch Pub the image of this bar is associated with the place “where everybody knows your name.” Even though I was too young to have watched all the episodes, the theme song is something I grew up hearing, which is why I proceeded to belt it out in the small lobby of the bar before the family walking out gave me a crazy look.

Next we decided to take a walk on The Freedom Trail. It’s kind of up to you where you’d like to start and what stops you want to make, which is what makes this fun. And the coolest part is it’s actually a physical red brick line that you follow down the street!

 

The trail is full of really interesting facts about the history of Boston. I like that you are able to follow the trail at your own pace, but feel free to book a tour. We heard some snippets from the tour guides along the way and they have a lot of amazing tid bits you otherwise wouldn’t get to hear.

We ended the day at America’s Oldest Restaurant, which is located on The Freedom Trail.

Union Oyster House– 41 Union Street

 

Check out the gigantic lobster they keep in the tank when you first walk in.

Tip: Make sure you are hungry when you come here. You are going to want to have room for the delicious homemade corn bread they bring out with warm butter. (YUM) & they keep it coming as long as you let them!

Unfortunately, by then it was time for our drive back to NY. But we were starting to miss our cat anyway!

All in all, Boston was so much more than we had ever expected. We would recommend it 10 out of 10 times and we can’t wait to go back & discover everything we missed!