10 Things You Can’t Miss in Boston

All I can say is wow! Boston exceeded my expectations and I honestly can’t wait to go back. It encompasses a healthy mix of modern and historic, but really the history is alive and so prominent here. I was pleasantly surprised at how relatively close everything was, how small the city “blocks” were, and how walkable the city was. Even in mid-December!

The people were charming, nice, and so eager to give you their favorite recommendations. You can tell the people of Boston REALLY love Boston. It’s also like a walking Instagram city. I am not lying when I say every place I walked into had so much charm and personality to it.  (This is also why I took over 1,000 photos while I was there!)

While I was only there for a long-ish weekend (4 days) I could have stayed there for a week and still not have run out of things to do and places to see! Even though I’m sure everyone would prefer to go in summer/fall for weather reasons, I was very happy to go in December. The city is decorated so beautifully with charming neighborhoods right around every corner. It’s like walking in your own personal Hallmark movie.

Since I did so many things in Boston that I simply can’t leave out, I’m breaking it down into 10 areas of Boston where you’ll find my favorite things..and food!


I wanted to start with Seaport as this is the area where we stayed. When booking our hotel, none of us had ever traveled to Boston before so we weren’t entirely sure where to stay! We decided to book at the Residence Inn in Seaport. It honestly was a great location, close to some amazing bars and restaurants, and in such a cute neighborhood. Not to mention how cute the hotel was too. Think exposed brick walls, high ceilings, and a decorated atrium. The funny thing is, Seaport was all but parking lots about 5 years ago and now its bustling! This area is very modern, but you still find the charm of brick sidewalks and old buildings.

My Top Places in Seaport:

  • Barking Crab-Located right on the water, it looks just like a crab shack. The clam chowder was of course delicious but, definitely go big or go home and order a whole lobster. They have 1.25, 2, 3lb and even 10 LB LOBSTERS! (Bring your wallet, hehe)
  • Row 34: Extensive beer list (really unique choices), great seafood and oyster bar options, and AMAZING lobster roll. We tried both naked and original styles.
  • Scorpion Bar- Doubles as a nightclub on the weekend & if you’re looking for modern Tex-Mex, come here for apps & a drink. The staff is super friendly, drinks are good, and they play great music!
  • Lucky’s Lounge- Divey- Sinatra themed bar. Live music on Thursday nights. This place is LIT! There was always a line to get in every night (albeit, short and you didn’t have to wait long) but it’s split into 2 parts with 2 bars. It’s fun, funky, and low key. Definitely, a must if you’re in the area.
  • City Tap: Tap house with great beer list, and a fun take on bar foods. Think corn and crab hush puppies, 10 spice wings (including sugar as one of the 10 spices), Clams casino pizza, and bacon & honey mussels.
  • Bartaco: a cute little place with great margaritas!
  • Committee: While we only popped in here to see how it was, this place was bustling, hip, and great to stop in for a drink or Mediterranean food! 

Top of the Hub | Prudential Center

If you have a night where you’re looking for amazing food, incredible views, and accommodating and attentive staff, be sure to book a table at the Top of the Hub located in the Back Bay area of Boston. Inside the Prudential Center, this restaurant sits on top of the Prudential tower on floor 52. It’s an unforgettable dining experience and great for a romantic date night too. (No romantic reservation for us; We celebrated my sister’s birthday!).  Start with a Cranberry Mule or Ginger Lemon Drop to accompany the lobster bisque or clam chowder and then dig into their scallops, duck, or lobster mac & cheese. You can’t go wrong with anything there! After dinner, peruse the Prudential Center as they have a ton of additional shops, restaurants, and bars! Ideal to explore if the weather is not so great outside.

Faneuil Hall | Quincy Market | Boston Public Market

I’m sure if you google top things in Boston any of these names come up. This area is pretty touristy and the time spent there can be as short or as long as you want it to be. Make sure to check out the big Christmas tree right in front of the Quincy Market (when in season). They do a light show every night to Mariah Carey’s ‘All I want for Christmas’.  Also around this area, you can find street vendors inside Quincy Market but also some typical chain shops as well. (Think Gap, Urban Outfitters, etc).

Walk into Quincy Market with an empty stomach! It’s a big food hall with a pretty dome in the center to sit down at eat. Try some clam chowder in a bread bowl, bacon wrapped scallops, gelato, Regina’s Pizza, a Boston dog.. the list goes on! Go with a group and get multiple things to share. Or just order a bunch for yourself..your secret is safe with me!

Head north on Union Street and you’ll see columns with steam coming up. That is the Holocaust memorial, and worth taking a peek at. It will give you all the feels.

Right past, you see the Boston Public Market. It’s similar to Quincy Market with multiple food establishments but a little bit more modernized. It’s a great option for something quick and cheap! They have a donut shop, popovers, a juicery, ramen.. you name it! We grabbed a few items from local vendors to nosh on when we went back to our hotel. While you’re over there you’ll see several bars along the way which brings me to the next things!


Bell in Hand | Union Oyster House | Green Dragon

After you’re done at Quincy Market or the Boston Public Market take a stroll through the alley, up the Freedom trail on Marshall street for some of the oldest spots in town. If you’re in the mood for a libation, make it a point to step into the oldest tavern in America where the first pour was back in 1795. Bell in Hand has a unique set up, making it have so many things to offer. We bellied up to the bar and had a hot spiked cider and my new favorite beer- Shipyard Pumpkinhead Ale and warmed up from the cold. They have 4 bars in this establishment, 2 on the main floor and 2 upstairs. Upstairs doubles as an event space, but also a dance floor on the weekends! Make it a point to check upstairs. (I snuck up when there was a private party going on so I couldn’t snap a photo, but the wall art was pretty sweet) They have food as well but if you’re hungry.. walk a few steps to EAT at the oldest Restaurant in the United States. 

Union Oyster House is a staple by far in Boston. It has the old charm and little dining rooms every which way. I popped in to check it out and the interior was super cool. Make sure to check out JFK’s favorite booth, coined “The Kennedy Booth”, where he always ate when he was in town. We ended up not eating here because it was a fairly long wait for a table. Instead, we found a divey-bar right around there called the Green Dragon. 

I’m not lying when I say this was my favorite bar in Boston. Not sure if it was the alcohol talking when I decided this, but the bartender was so pleasant. Typical Boston accent, a little rugged around the edges, but one of the sweetest bartenders ever. We had a grand old time drinking the Shipyard Pumpkinhead Ale again and enjoying everyone’s company. 

PS, the little alleyway that connects these bars makes a great photo op! Make sure to see the “Boston” mural along the one side at the back of The Point. See photo below! 

Trolley tour

If you have a day where the weather isn’t exactly favorable, consider taking a trolley tour! I’m a huge fan of hop on hop off tours ANYWHERE I go. I honestly think it’s the easiest and quickest way to see all the sights when you’re traveling.

We decided to do tickets with the CityView Trolley Tour. With only 8-9 stops it’s actually one of the quickest trolleys in Boston. Some stops are within walking distance too. For example, Stop 1 and Stop 6 are only a few blocks apart.  The day we went was the coldest day there and very windy, so needless to say, we stayed on the trolley for a good amount of time.

EJ, our tour guide, was so hilarious and informative and created an all around good time! You learn so much just looking out the trolley and listening to the history.  Boston has several options for trolley tours but we were happy with this choice of trolley. If you’re looking for a longer one that heads in to Cambridge, definitely check out the Old Town Trolley Tour that has 18 stops.

Boston Common

When we finally decided to “hop off’ we landed in Boston Common. Think of it as the Central Park of Boston. This time of year you’ll find the park colorfully lit with Christmas lights, and a pop-up ice skating rink too!

Another fun fact, this is the oldest city park in the United States, dating back to 1634. Definitely do some reading up on this park as it’s history is extremely rich. George Washington and John Adams went there to celebrate our nation’s independence, Martin Luther King, Jr. held civil rights rallies, and Pope John Paul celebrated mass there in 1979. If that doesn’t do anything for you…it really is a great location anyway as its bounded by Beacon Street, Boylston Street, and Park street, all which have so many sights to see!

Beacon Hill | Acorn Street

Head north of the park to Beacon Street. You’ll find the cutest front stoops but also the iconic Cheers sign! Spoiler alert.. the show was not even filmed here if you did not know. If you are here, take a quick a picture and continue on. It’s nothing worth noting to be honest and a huge tourist trap! Instead, take a turn onto Charles Street and take a stroll through Beacon Hill.

Beacon Hill is definitely where I felt I was in my own Hallmark movie! The cutest little stores, restaurants, and cobblestone streets..I was in my own little heaven! Pop into the stores and shop the merchandise. Everything is very unique and not like other stores I’ve been to. The street is lined with so many quaint restaurants and pubs too. We decided to check out Figs to warm up with a glass of wine. If you’re in the mood for pizza while over there, make sure to order their brick oven pizza; we sat at the bar and watched the chef cook pizza continuously and our mouths were watering the whole time!

If you’re adventurous, take a gander through the side streets of Beacon Hill and you’ll actually come to one of the most Instagrammed places in Boston: Acorn Street. You’ll be shocked at how small it is when you arrive but you’ll know you’re close if you see everyone with cameras nearby. It’s a great hidden gem in the neighborhood. The door fronts are picturesque especially now for the holidays – It’s also one of the most beautiful Colonial streets in Boston. Just please be courteous to the residents living there. It wasn’t an issue when we were there but I’ve heard worse!

North End

If you like Italian food, you better make lots of time to hang around Boston’s North End. Coined the “Little Italy” of Boston, this small Italian neighborhood place has not only great food but also some great history too! Come here to see Paul Revere’s house, the Old North Church, and also the Paul Revere Statue. Walk up and down Hanover street and attempt to settle on a restaurant.. it’s harder than you think. We dined at Florentine’s but I’ve also heard amazing things about Limoncello as well. You can’t go wrong when the pasta is made fresh daily from scratch.

After stuffing your face with pasta, make sure to leave room for a cannoli! Try and settle the debate on whether Modern Pastry or Mike’s serves the best cannoli’s in town. I’ll leave that debate up to you. 🙂


If you have time, take a quick Uber over to the Cambridge area. Yes, we were touristy and walked around Harvard but honestly, it was pretty incredible. We walked through Harvard Yard and perused through Harvard Square amongst students, parents, tourists, you name it. It has such a cool energy over there and the buildings alone are breathtaking. And if instead, you’re using public transit, it’s so easy to get there via the red line!

A different night, my boyfriend and I actually caught a show of a favorite artist, Roosevelt, who was playing in town in the Cambridge area. We went to the Middle East- Downstairs. I honestly had no idea what to expect as when I googled it, it literally came up as a restaurant’s basement. I was a little nervous if I’m being honest here. However, once in, (after some pretty heavy security for a basement venue) It was actually pretty cool! It’s definitely dive-y and grungy but honestly, it was so much fun! If there’s a DJ spinning there one night, it’s worth to check it out.

USS Constitution

Do you like history? Do you like Ships? Then you gotta check out the USS Constitution at the Charlestown Navy Yard (or also known as the Boston navy yard). This historic site is actually administered by the National Park Service making it a National Historic Park. Wednesday through Sunday the navy yard runs free tours every 30 mins aboard the USS Constitution or “Old Ironsides” if you will. I’m not a huge history buff or ship nerd but I’ll admit, this was pretty cool walking aboard the oldest warship still commissioned in the US Navy. Within the tour, you can walk along the deck and even go deep into the ship. But, beware if you are tall! It’s incredibly small and tight once you start walking down!


I hope you enjoyed reading along with my Boston Travels. There are so many things still on my list for when I return but if you hit any of these areas, you are bound to have a good time. Happy Travels!

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