A Weekend Guide to Boston

A Weekend Guide to Boston

Boston is a city overflowing with history and culture. I am sure we have all heard of the Boston Tea Party and are aware of the great historical impact Boston holds for our nation, but Boston is so much more than that. It has a rich music scene, an endless variety of cuisine, prominent educational institutions, and diverse neighborhoods that each offer their own unique charm.

And to be honest, all that may seem a bit overwhelming, especially when exploring a city you have never been. You want to be sure not to miss any of important spots, right? Well you are in luck!

Below I have compiled a guide of things you must see, do, and eat during your weekend getaway to Boston.



If you know anything about me, I love food. More specifically, I love brunch food. Therefore, if you are in the mood for some delicious and unique brunch cuisine, I know two great spots for you to try

Lincoln Tavern


First of all…how cozy is this setting? It is the perfect retreat from the winter cold. Not to mention their food is absolutely scrumptious. I recommend going for Friday brunch. On Fridays, Lincoln Tavern has what they call their “test kitchen,” this means that new items are added to the menu for one day, and one day only. So if you are a foodie who is feeling adventurous, this is the place to go!

Pictured Left: The breakfast pizza. It was sensational! I mean pizza is incredible in and of itself, then you add breakfast food to it (like hash browns and eggs), and you have a golden pie of heaven.

Pictured Right: The french toast. I think this picture speaks for itself. Oh, and did I mention there is bacon mixed in there. No? Well how silly of me…cause there is…and it is epic!

The Gaslight

Located in the South End of Boston (my absolute favorite end of Boston), is a charming French restaurant called The Gaslight Brasserie. The Gaslight offers up that classic French charm and finesse you would expect and delivers cuisine that emanates French refinement.


I recommend making it in time for the prix fixe brunch. For $11.95 you get your choice of fresh squeezed orange juice or grapefruit juice, a slice of Julia Child’s spice shortbread with raspberry jam, and your choice of one entree. The entrees include french toast, varying omelettes, and crepes.

In order to make if for the prix fixe brunch, you must go Saturday between 9:00am-3:00pm and Sunday 9:00am-11:00am.

Then once you finish brunch, take a stroll down the charming streets of the South End. The classy town homes and countless art studios (which you are allowed to tour) had me geeking out nonstop. It is safe to say that the South End is my favorite part of Boston.


James Hook 

Now when it comes to lunch, there is one place I highly recommend. This place is known for their lobster and they happen to provide lobster online with overnight delivery in the U.S.. From the ocean to your front door (that should be their new catch phrase).


This place also happens to sell one of Boston’s most classic and iconic dishes: the lobster roll. Do not let the $20 price ticket defer you, it is worth every penny.


Before heading to Boston, one of my bucket list items was to try a lobster roll. Not only did I get to check that off the list, but I also discovered a new found passion for the dish. I mean, just look at the juicy-ness pictured above. Delicious. That is all I can say. The luscious lobster, paired with the buttery bread, and creamy sauce…it’s a perfect harmony of flavors in your mouth.



Legal Harborside 

Everyone knows that Boston is famous for its seafood, and there is good reason for that. Their seafood is extremely fresh. You can literally stare out at the water where your food came from as you put it in your mouth.


To fill that seafood craving, Legal Harborside is the perfect dinner spot for your first night in Boston. With a huge menu and three separate dining floors, each offering unique amenities, you can be sure to find just what you are looking for.

Pro Tip: Order a cup of the clam chowder, it is a must!

Lolita Cocina

I am so sad I didn’t get any good pictures of this place. But even so, I couldn’t not put this on the list, it is just too insanely cool!

The atmosphere is a weird combination of gothic meets Mexican. It is like nothing I’ve ever experienced. To give you an example of how insanely cool it is, for dessert, they give you homemade cotton candy. Who does that?! Therefore I will just say this, you need to experience this place for yourself.

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Photo Via: Bergmeyer

If the above information hasn’t convinced you yet, then you should know that their food is equally as amazing. I mean, Mexican food is pretty much our nation’s comfort food (or at least mine). And any restaurant that provides complimentary chips and salsa earns a special place in my heart.


The Green Dragon Tavern

Calling all history buffs! If you love history and pub food, this is the place for you. Established in 1654, The Green Dragon Tavern has a long and rich history. Not only is it known for playing a major role in the freedom of Boston during the  War of Independence, but it also was a favorite spot of Paul Revere and John Hancock.

As if that is not cool enough, it was at this very pub that the plans for the invasion of Lexington and Concord were overheard, initiating the famous ride of Paul Revere.

All that said, this place makes you feel as though you stepped back in history. In order to get to the tavern, you must turn of the street and walk down a cobblestone alley. You will be greeted at the door by this soldier statue. Once you see him, you will know you have made it.


Mike’s Pastry

Known for their cannoli, Mike’s Pastry is located in Boston’s North End. The North End is known for its rich Italian heritage, which is quite evident as you walk the streets. A never ending stream of Italian joints line each avenue, the smells of ravioli and risotto linger in the air.  I recommend making the North End both a dinner and dessert stop one evening.


Established in 1946, Mike’s Pastry is a North End Tradition, which probably explains the chaotic mass of people filling the small shop to capacity. My advice, be prepared for a lively atmosphere! Everyone touring Boston wants to get their hands on one of those yummy, crunchy, and creamy creations.


If you are not a cannoli fan, there are countless other pastry items filling Mike’s glass dessert cases. Take your pick. Anything you choose is bound to be delicious.


Trolley tour


If you want a historical tour of Boston but don’t want to do all the walking, a trolley tour is the perfect option for you. There are a few different trolley options, but I would recommend Old Town Trolley Tours. With your full-day ticket, you can hop-off at 18 different stops and then hop-on whenever you are ready to go to the next one.

Tickets tend to be a little pricey, at $44.05 per ticket. But remember, it is good for the entire day and provides you with a historical tour of Boston, while taking you to 100 points of interest. Added bonus: the tour guides are hilarious!

Quincy Market 

Marvelous. This place is just marvelous.

The area surrounding Quincy Market is lined with brick roads and encircled with refurbished buildings containing popular shops. It is a mix of old, classic Boston charm meets modern-day consumerism. This is definitely a place to visit if you are a shopaholic or a foodie.


Forewarning: If you are an indecisive person, this is not the place for you. Once you step through the great doors of Quincy Market, you enter a long hallway lined on both sides with a variety of food shops. Serving up a smorgasbord of international cuisines and local snacks, this place has a little something for everyone.


Towards the middle of the market, is a large, open food court area, where you can sit and rest for a minute, enjoy the trays of food you collected, and get your energy up for round two.

I should also mention that within the walls of Quincy Market you can find the Cheers restaurant. I myself am a big fan of the show, so when I found out, I fan-girled pretty hard. However, it should be noted that this is not in fact the bar where the show was filmed. The actual Cheers bar can be seen on the Boston trolley tour.

Newbury Street (Back Bay):

The enchanting Newbury Street can be found in Boston’s Back bay. Eight blocks filled with boutiques, salons, and posh dining, it has a little something for everyone.

As you walk the classy sidewalks of Newbury Street, you might need a little something to warm you up. For that, I have just the place! L.A. Burdick is an adorable chocolate shop, serving up handmade chocolates and the richest hot chocolate my lips have ever touched. YOU HAVE TO TRY THEIR HOT CHOCOLATE. It is as if you are drinking a melted chocolate bar…and its as amazing as you’d think it would be!

It should be noted that Berklee College of Music can be found in this area, as well as Boston Public Library.


The Boston Public Library was established in 1848 and was the first free municipal library in the United States. I highly recommend stopping inside! The architecture is breathtaking, simply breathtaking. With delicate attention to detail and marvelous artwork, it is a must-see.

Harvard University

When coming to Boston you have to see Harvard…it is just something that needs to be done. And trust me, it is worth it.

The school has maintained its historical feel, with cobblestone streets, charming buildings, and that old-city charm. I’ll admit, just walking on the historical and prestigious campus made me feel 10x smarter.



If you are looking for a place to stay, I would strongly urge you to find an Airbnb. I cannot rave about Airbnb enough! Our Airbnb was an adorable apartment 4 miles from the city. The host was great and it slept 6 of us comfortably!


So there you have it folks, my guide to a weekend in Boston. Please like and share the post if you found it helpful! And I would love to hear any comments or recommendations you might have. Thank you for reading 🙂

If you enjoyed this post, you may like The Ultimate Food Guide to Athens, GA or A Weekender’s Guide to Nashville, TN.

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