48 Hours in Boston | What to See & Where to Eat

I just recently came back from a trip from Boston, and I can say that I could see myself living there in the future! It has a city vibe, but isn’t too overwhelming like how New York City can be sometimes. Here’s where I ate and what I did in 48 hours in Boston- besides the Freedom Trail. Not saying you should skip the Freedom Trail, but there is so much to discover beyond it!

Boston Common and Garden

48 Hours in Boston: Day One

Arriving into Boston by Bus

Did you know you can take a bus from New York City into Boston for $30 round trip? Ever since traveling around Europe, I learned that flying sometimes can just be inconvenient with all the extra time associated with checking in and waiting around. Depending where you are traveling from, you can reach Boston by bus or train if you are in the Northeast. I find this a great alternative to flying.

There are many bus companies that offer services into Boston including: Bolt, Big Bus, Greyhound, and Peterpan. However, I always had good experiences on Bolt Bus, as I feel their fleets are cleaner. The drive takes about 4.5 hours which may seem like a lot, but I bring either a book, or work on my laptop. Soon enough you will arrive into the center of Boston at South Station.

Bolt Bus to Boson

Air B&B Check In

One thing about Boston is the hotels are quite expensive, $250+ a night in the center of the city. Since we were here for one night we decided to stay in an Air B&B. The studio was a great value at $130 a night and was in the center of the picturesque residential neighborhood of Beacon Hill.

Exploring Beacon Hill

Get out your cameras! This 19th century neighborhood is the cutest neighborhood in Boston by far. Gorgeous town homes line the narrow cobblestone streets that are lit by gaslight lamps! At night it’s just dreamy! It’s also named Beacon Hill for a reason- it was built on a large hill so beware when walking you will see a lot of uneven cobblestones!

To get a little history out of exploring this neighborhood you can do a self guided walking tour, or you can just explore the streets yourself. If you do explore yourself make sure to check out these adorable locations: Rouvalis Flowers, Louisburg Square, and Acorn Street.

Rouvalis Flowers: Charming flower shop with a cute outdoor selection of seasonal flowers and plants.

Louisburg Square: Quiet square in the center of Beacon Hill. Was admiring the open space and greenery among the stunning homes!

Acorn Street: One of the most photographed streets on America! You can step back into 19th century colonial America with a steep uneven stone street and beautiful row homes!

Boston's Acorn Street Boston's Acorn StreetBoston's Acorn Street

Tip: Early morning seems to be the best time to take photos to avoid anyone in your picture!

Lunch at Tatte Bakery & Cafe

Calling all Instagram Foodies… Tatte is the place for you, filled with fresh pastries on display, seasonal tarts, cookies and cakes! The light and airy cafe also has a lunch menu featuring unique salads, sandwiches, and warm bowls. We went to the Charles Street location in Beacon Hill that also has an outdoor patio. I loved the warm and homey feel this place provided and the Warm Farro & Vegetable bowl was delicious!

Tatte Bakery Boston

Tatte Bakery Boston

Walk through Boston Common & Public Garden

Even though November isn’t the warmest time to visit Boston, seeing the trees change color is totally worth it! The red and golden hues were so pretty! Of course you can just enjoy the park yourself, but if you wanted to check out things to see in the park here is a nice guide!  I certainly loved the piles of leaves, and the gorgeous pond!

Boston Common and Garden

Boston Common and GardenBoston Common and Garden

Drinks at Liberty Hotel

After relaxing in the park we walked to the Liberty Hotel. This hotel used to be the Suffolk County Jail and now it’s turned into luxury hotel. The restaurants and bars inside have adapted the theme with jail bars on the windows and notorious mug shot photos. We came around 4PM so some of the bars weren’t open yet, so we had a drink in the gorgeous lobby! I imagine at night and on the weekends the hotel bars can become pretty crowded with an overall upscale vibe.

Liberty Hotel Lobby

Unique Dinner Experience at Lolita’s

After doing my Boston research, Lolita’s Cocina & Tequila came up on nearly all reccomendations. As ZAGAT described it as: “hopping Back Bay Mexican is the “place you want to be” for “tasty” eats, “to-die-for”margaritas and “little extras” that fuel the “really funky vibe”That being said I had to check it out! We were apprehensive wondering if it would be even busy on a random Tuesday in November, but lo and behold once we walked in we had to wait over an hour for a table! It was buzzing with great energy.

Reccomendations: We absolutely loved our drinks; the Spicy Cucumber Margarita was tasty and strong. To eat we devoured the tuna tar tar and the shrimp tacos! This place is perfect for a nice night out, birthdays, or a date spot! I really had a great time!

Tip: To avoid a wait, make a reservation- even if it is on a weekday.

Lolitas Boston

48 Hours in Boston: Day Two

Tour of the Boston Public Library

Did you know that the Boston Public Library was the first Library in the USA to be free for everyone? We took a free art and architecture tour of this gorgeous historic building. You can find tour times here as they change on different days. We learned about the details of the building and it’s history. If you have some time in Boston and are interested in art, I would recommend the tour! Other wise, to see the beautiful Instagram famous study room, just head to the second floor!

Boston Public Library

Coffee & Wine Break at Jaho

We took a quick break at Jaho, a local Boston chain that is both a coffee shop and wine bar. It was perfect because I wanted a Cappuccino and Alsenio wanted a glass of wine. We took a little rest as we planned the rest of our day.

Jaho Boston

Sifting through Brattle Book Shop

Just around the corner from the Boston Opera House, is Brattle Book Shop. It is an antique book shop that offers used books in the abandoned lot next door. I loved the art mural of the famous writers. If we had more time I would have loved to sift through and find a nice book, but in the mean time we just took some photos!

Brattle Book Shop Brattle Book Shop

Walked through Little Italy & Visited Paul Revere House

We then walked to the North End of Boston, also known as Little Italy. On the way we passed Faneuil Hall Hall and Quincy Market. It’s a typical tourist attraction apart of the Freedom Trail. If it’s your first time to Boston, of course check out these buildings, but in terms of a food selection you are way better off finding something outside of this tourist area.

North End Boston North End Boston

Paul Revere House

Little Italy has historic architecture including the Paul Revere House. We went in and toured the house for $5. It was home Paul Revere built in 1680 featuring some of the original wood work! The house is small so you won’t spend too much time here, but I always love going inside old homes to see how the architecture has changed throughout the years! There are also two knowledgeable employees in the home you can ask questions to about the furniture, lifestyle of the time, or anything you can think of.

Paul Revere House

Sunset Watching over the Harbor

We watched the sunset over the harbor, but in the past I have taken a sunset tour on a boat around the harbor. They only offer this in the warmer months of Boston, but if you are visiting in Summer check out: Boston Harbor Cruises.

Dinner in Little Italy

The North End in Boston has the best Italian food in Boston. We went to Giacomo’s a family owned down-to-earth restaurant with home made pasta and fresh seafood. I have been here in the past and had to wait in line! This place gets packed, so either come early or just before closing otherwise expect a line. However, the aroma of garlic and fresh pasta is completely worth the wait.

Tip: Cash Only

Giacomos Boston

Bus Back to New York

After dinner, we picked up our luggage from the Air B&B and headed to South Station. Overall we had a great time in Boston, with cool sunny weather! Everywhere we went I recommend, but my highest reccomendations are eating dinner at Lolita’s, and exploring Beacon Hill. Things to skip: eating at Quincy Market, it’s filled with chain restaurants- go explore the neighboring North End and eat something authentic Italian!


This concludes our 48 hours in Boston! If you enjoyed this guide: check out my other guides like my Girls Guide to Miami!

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48 Hours in Boston


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