I’m going to go out on a limb and say this, but even though I’m a New Yorker, Boston might be my favorite Northeast city and after spending 2 Days in Boston this Summer I can confirm that it is the BEST!
Just in case you didn’t know Boston is located in the state of Massachusetts and is the largest city in the New England region of the country. It’s known for it’s rich American history (like it being the first Puritan settlement and home to many of the key events of the Revolutionary War), beautiful neighborhoods (Beacon Hill is my person favorite), fresh seafood and much more!
There are so many things to do and see in Boston that you could easily spend a week there and still not be done exploring, BUT it’s also not too overwhelming of a city and is perfect for one of your Summer or Fall weekend getaways. Even as a first time visitor you’ll easily be able to navigate the different neighborhoods by foot or by using public transportation (Fun Fact: the T, Boston’s subway system, was the United States’ first subway system).
Since Boston is just over a 3 hour drive from Westchester County, New York I’ve visited multiple times, but since we were with Simone, who has never been to Boston, we hit a lot of the attractions that one would want to visit if it was their first time in Boston!
As always I’m giving you my exact 48 hour Boston itinerary so if you want to visit you can see how much you can actually fit into each day, then I included the best things to do, see and eat in Boston on the bottom along with a few other recommendations on where to stay when you’re visiting.
2 Days in Boston Itinerary:
We left Westchester around 10am on a Friday and hit a little bit of traffic on our way to Boston so we arrived right around 1:30pm and fortunately were able to check right into the Boston Park Plaza, where we were staying for the weekend (sharing a little more about the hotel on the bottom of this post).
After quickly checking in we walked over to The Banks Fish House for lunch to kick off our 2 days in Boston (or what you’ll soon realize should be called 2 days eating around Boston). This is a relatively new Boston restaurant in the Back Bay neighborhood, but once we saw the menu and the stunning decor we knew we needed to check it our and it didn’t disappoint! We sipped on Prosecco while enjoying Unicorn Oysters, Fried Artichokes, Steamed Mussels, a Lobster Roll & The Chowda Flatbread!
After lunch we wandered around Back Bay and over to Boston Common Park, a must see if you’re visiting Boston. Make sure you check out the Public Garden, Swan Boats, the George Washington Statue among many others in the park.
We exited out the north side of the park near Cheers (cute to walk past, but in my opinion not worth going to unless you’re a huge fan of the TV show) and walked around Beacon Hill, my personal favorite neighborhood of Boston.
Beacon Hill is filled with elegant town houses, narrow brick streets with working gas lamps, local boutiques and tiny restaurants.
Overall it’s PICTURE PERFECT, and extremely Instagrammable, and not to be missed if you’re in Boston. Make sure you stop by Acorn Street while you’re there to snap a photo. This famous street is the MOST PHOTOGRAPHED street in American and a must see!
We headed back to our hotel after walking around Beacon Hill to change for dinner at Bar Mezzana in Boston’s South End’s Ink Block Neighborhood. This restaurant was highly recommended by multiple people so it was a must visit for us! Order the Rosemary & Onion Focaccia accompanied by Eggplant with Chili, Honey & Goat Cheese, Peperonata and White Beach Puree with Rosemary & Tahini to start. Then split the Prosciutto di San Daniele, Black Truffle Burrata, Paccheri with Lobster and Orecchiette.
We started the morning with coffee and pastries at Tatte Bakery, a MUST VISIT if you’re in Boston. We literally went 3 times in the 2 days we spent in Boston and basically begged them on social to open a location in NY. There are multiple locations throughout the city so no matter where you stay you can start your morning there.
If the black and white aesthetic isn’t enough to get you to visit, the BEYOND delicious pastries will. The pistachio croissant was quite possibly in the top 5 things I’ve ever eaten and I haven’t stopped thinking about it since. I also highly recommend the pistachio donut and literally ANYTHING else you can get your hands on there.
After breakfast we started walking towards Downtown and Boston Harbor. We made sure to stop at Brattle Book Shop, Old State House, Quincy Market and Faneuil Hall. Then we made our way down to Boston Harbor for a little before lunch.
We walked over to Boston’s Seaport District for brunch on the water at Woods Hill Pier 4.
It was 95 degrees out so we all ordered Frozé that was delicious and perfect to cool off with. Then we split the Salad of Mixed Greens with Grilled Chicken, Heirloom Tomato Salad, WHP4 Burger and the Lobster Popover. ALL insanely delicious.
After lunch we took a LYFT over to the North End, Boston’s Italian neighborhood, to eat cannolis, because you can’t go to Boston and not eat a cannoli or two in Boston’s own Little Italy. Tourist favorite is Mike’s Pastry, but the local favorite is Modern Pastry. We got both obviously and while Modern is more authentic, I enjoyed Mike’s a little better! If you’re headed to Boston I would get a cannoli from each place and try it yourself.
Then we headed back to the hotel to change and off to dinner at Saltie Girl. Another highly recommended restaurant that we got a last minute reservation at and were SO happy! Order the Clam Chowder, Snow Crab Toast, Torched Salmon Belly, Warm Spicy Crab Roll, Hand-Chopped Dry Aged Steak Tartare, Rock Crab Carbonara and Ginger Scallion Lobster.
We checked out of the hotel and headed back to Tatte Bakery because we couldn’t get enough of it and walked over to the Boston Public Library in Copley Square. Unfortunately it’s closed on Sundays so we couldn’t go in, but if you’re in the area on another day of the week add it to your itinerary.
From there we hopped in a LYFT and headed to Lolita Cocina & Tequila Bar in Fort Point for brunch. Make a reservation inside because the gothic, dark decorated space is not to be missed. Order the Guacamole Fresco, Mushroom Empanadas, Tuna Maracuya, Lolita Lobster Roll (topped with Mexican corn!), Mushroom Quesadilla and Broken Eggs.
After brunch we walked through the Boston Seaport on the Harborwalk to snap some photos of the Boston Skyline and then were headed back to the hotel to hit the road to our next location.
Things To Do In Boston:
Walk the Freedom Trail
The 2.5 mile long path goes through 16 locations significant to the history of the United States. The trail is marked by red brick and starts in Boston Common and ends at Bunker Hill Monument in Charlestown. It’s a great walking tour to take because it brings you past all the can’t miss historic places in Downtown Boston like the Old State House, Old South Meeting House and Paul Revere House.
Boston Tea Party Ships
If you have kids with you I highly suggest heading to Boston Tea Party Ships & Museum. We walked past the re-enactment when we were in the Seaport and it looked like such a fun activity for kids – they actually get to toss “tea” off the full scale replica 18th century sailing vessel.
Sam Adams Brewery Tour
Located in the heart of Jamaica Plain, The Boston Brewery is the original home of Samual Adams. Book your Brewhouse Tour here and while you’re there make sure to enjoy a beer or two at the Tap Room or Beer Garden.
Go to a Red sox Fenway Park
Even if you’re not a Boston Red Sox fan I highly suggest going to a baseball game at Fenway Park. I was lucky enough to catch a Red Sox v. Yankees game a few years ago and it was awesome. The stadium itself is the oldest active stadium in Major League Baseball and one of the most well known sports venues in the world.
Eat Cannolis from Mike’s Pastry & Modern Pastry in the North End
Taste test cannolis from tourist favorite, Mike’s Pastry, and local favorite, Modern Pastry in the North End. Both of these long time family owned pastry shops are staples in the well know Italian neighborhood and it’s fun to try them both and see which ones you prefer.
Places To See In Boston:
Boston common park
Established in 1634, Boston Common is America’s oldest public park and hard to miss in the center of Boston. Don’t miss the Public Garden, Swan Boats and the statue of George Washington.
Beacon Hill Neighborhood & Acorn St
Beacon Hill is my absolute favorite area of Boston and for good reason. It’s picturesque and filled with elegant town houses, narrow brick streets with working gas lamps, local boutiques and tiny restaurants. It’s also home to Acorn St., the most photographed street in America.
Cambridge & Harvard University
Cross the Charles River and explore Cambridge, MIT and Harvard University. I haven’t quite made it to any of these places yet, but thats just another reason to go back to Boston.
Boston Public Library
Like I mentioned in my itinerary we didn’t get a chance actually go into the Boston Public Library because we went on a Sunday and they’re closed, but it’s definitely a place to see.
Places To Eat In Boston:
- Located in Boston’s Back Bay Neighborhood
- The decor is ON POINT, highly recommend visiting for lunch so you can see it all in the light
- Has a large bar & a separate oyster bar
- Recommended Dishes: Unicorn Oysters, Fried Artichokes, Steamed Mussels, a Lobster Roll & The Chowda Flatbread!
- Reservations accepted
- Located in Boston’s South End Ink Block Neighborhood
- Indoor and outdoor seating available
- Recommended Dishes: Rosemary & Onion Focaccia accompanied by Eggplant with Chili, Honey & Goat Cheese, Peperonata and White Beach Puree with Rosemary & Tahini. Prosciutto di San Daniele, Black Truffle Burrata, Paccheri with Lobster and Orecchiette
- Reservations accepted
- Multiple locations around Boston
- Indoor and outdoor seating available
- Fast casual – you order at the counter and they bring your order to your table or you can order to-go
- You MUST get the Pistachio Croissant – it was the best pastry I’ve ever eaten
- Located in the Boston Seaport District
- Indoor and outdoor seating available with harbor views
- Recommended Dishes: Salad of Mixed Greens with Grilled Chicken, Heirloom Tomato Salad, WHP4 Burger and the Lobster Popover
- Reservations accepted
- Located in Back Bay right off Newbury St
- The inside decor is a pink dream! Every inch of this restaurant is beautiful and so eclectically decorated
- Reservations accepted and make they’re not very easy to come by! Make one the second you know you’re headed to Boston.
- Located in Fort Pierce
- Highly suggest going there for brunch, but I imagine that dinner is also amazing there
- Get a table inside because the gothic, dark decorated space is not to be missed.
- Order the Guacamole Fresco, Mushroom Empanadas, Tuna Maracuya, Lolita Lobster Roll (topped with Mexican corn!), Mushroom Quesadilla and Broken Eggs.
- Reservations accepted
The next few we didn’t get a chance to eat at, but were highly recommended:
- Mariel – Cuban food with amazing drinks
- Bootleg Special – Seafood and crab boils with Mardi Gras inspired cocktails
- Yellow Door Taqueria – Best tacos and margaritas
- Committee – Cocktail menu is one of the best in the city with incredible Greek food
- Rowe 34 – Go to for oysters and lobster rolls
- Coppa – Charcuterie board masters
- Source – Best pizza located in Harvard Square
Places To Stay In Boston:
- Centrally located in Boston’s Back Bay and steps away from Boston Common and the Theatre District
- Originally opened in 1927, the contemporary design complements the original historic details of this hotel
- This is where we stayed during this trip!
- The central location of The Newbury at the intersection of Newbury and Arlington Streets makes this hotel iconic with Boston Public Garden across the street.
- First opened as the Ritz-Carlton, later as The Taj and now The Newbury Boston.
- Recently named one of the best new hotels in the world by Travel + Leisure magazine.
- Located in Beacon Hill
- Formerly the Charles Street Jail, the Liberty Hotel is a national historic landmark and architectural gem built in 1851
- Rooms have views of the city skyline and Charles River
- 5 star hotel located in the Financial District
- Formally the Federal Reserve Bank of Boston, The Langham has a 1920s heritage and is among the city’s most beautiful luxury options
- Located in Boston Harbor, the Boston Harbor Hotel is Boston’s only waterfront Forbes Five-Star and AAA Five-Diamond Hotel.
- This luxury hotel offers a full-service spa, swimming pool and modern gym among other amenities.
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