Boston is the biggest city in New England, and we’ve been living 40 minutes south of it for the past few months, so we figured it was finally time we pay it a visit! The awesome hosts we’ve been living with in Mansfield, MA actually grew up in Boston, so they were very kind and gave us a personal tour of their old stomping grounds. Boston is split up into several neighborhoods, so I figured I’d snap a photo of this cheese tray we used for Thanksgiving to better orient you as we take you through a very busy Saturday in the capital city of Massachusetts!
Boston Neighborhoods
Jamaica Plain
Our early morning tour mostly consisted of first driving around West Roxbury where our host family used to live so we could see their neighborhood. We didn’t have time, but they told us the Arnold Arboretum of Harvard University was a fantastic place to jog or bike through. Next, they drove us up to Jamaica Plain (a.k.a. J.P.) where they dropped us off in the cute downtown area on Centre Street. Our hosts recommended J.P. Licks for breakfast, which is actually most known for their ice cream, so naturally we had to get mocha milkshakes with our breakfast sandwiches to start our day! We enjoyed sipping our milkshakes by the fireplace until the bakery “When Pigs Fly” opened at 10 a.m. We arrived at 9:58 a.m. right when they were opening the door and we were lucky to be the first ones to order because when we walked out, the line was already out the door. Apparently on Saturdays “When Pigs Fly” has giant donuts and they only have a certain amount, so when they sell out, they are gone! We actually opted for the tasty fresh baked cookies instead of the donuts. You can’t go wrong!
Downtown Jamaica Plain
J.P. Licks
Mocha Milkshakes for breakfast!
When Pigs Fly
Giant donuts and other tasty baked goods!
Downtown Jamaica Plain
J.P. Licks
Mocha Milkshakes for breakfast!
When Pigs Fly
Giant donuts and other tasty baked goods!
Sam Adams Brewery
After enjoying our two-course breakfast, we walked about a mile east to the Sam Adams Brewery still in Jamaica Plain but on the fringe of Egleston Square. We had booked a Morning Mash In Tour ahead of time for $16.82 online. We arrived a few minutes early for our 10:30 a.m. tour, so we perused the awards Sam Adams has won over the years while waiting to start. The tour was pretty standard- they talk about the ingredients, they show you the process of how they make their beer, and then they give you some samples. But I must say, our tour guide really made this tour awesome! He had our whole group laughing! We enjoyed our time here and it was fun to try some staples and some new beers!
Sam Adams Brewery
Sam Adams Tour
They’ve gotten plenty of awards!
Where the magic happens!
Where the tasting happens!
Can you tell we’re from Minnesota? 🙂
Sam Adams Brewery
Sam Adams Tour
They’ve gotten plenty of awards!
Where the magic happens!
Where the tasting happens!
Can you tell we’re from Minnesota? 🙂
Back Bay
After enjoying some late morning beers, we walked to the Green Street T station where we caught the orange line to Massachusetts Ave. We hopped off the T in Back Bay in order to stroll by a few skyscrapers. We took our stroll indoors when we hit the Prudential Center (the Pru)- and its seemingly endless swanky mall that weaves through the start of downtown.
Back Bay Neighborhood
The Prudential
The Prudential Center
Back Bay Neighborhood
The Prudential
The Prudential Center
The Freedom Trail
Big buildings are cool and all, but the true charm of Boston is the history. Our next stop was the Freedom Trail. The Freedom Trail is a 2.5-mile brick marked walk through downtown Boston that takes you to 16 marked historical sites from the Revolutionary War era. The trail starts in the Boston Common which is America’s oldest public park; you can find the start of the red brick in the northeast portion of the park. You will see people dressed up in Revolutionary War garb giving tours, but we opted to do a self-tour and utilized the online guide.
Boston Common
A skating rink in the middle of Boston Common!
The start of the red brick line marking the Freedom Trail.
The second site on the Freedom Trail: the Massachusetts State House.
Another Freedom Trail site: the Granary Burying Grounds where Sam Adams, John Hancock, Paul Revere, and more are buried.
This is how the Freedom Trail is marked throughout the city!
The Hop On Hop Off Trolley Tour that is a great option if you don’t want to walk to all of these sites.
The site of the Boston Massacre.
The Old State House is the oldest surviving public building in Boston.
Boston Common
A skating rink in the middle of Boston Common!
The start of the red brick line marking the Freedom Trail.
The second site on the Freedom Trail: the Massachusetts State House.
Another Freedom Trail site: the Granary Burying Grounds where Sam Adams, John Hancock, Paul Revere, and more are buried.
This is how the Freedom Trail is marked throughout the city!
The Hop On Hop Off Trolley Tour that is a great option if you don’t want to walk to all of these sites.
The site of the Boston Massacre.
The Old State House is the oldest surviving public building in Boston.
Quincy Market
Just past Faneuil Hall, you will find Quincy Market, a building filled with all sorts of food. The surrounding area has endless shops and they go all out with the Christmas decorations in this area! It’s definitely a lively area with street artists, performers, and live music.
Quincy Market
Inside of Quincy Market
This area is festive both inside…
…and out!
Quincy Market
Inside of Quincy Market
This area is festive both inside…
…and out!
The North End
About halfway into the Freedom Trail we ran into the North End Neighborhood. This is where you can find all the amazing Italian food and there are definitely no skyscrapers here! We wanted to choose two pizza spots and two pastry spots to compare. We tried Galleria Umberto, a hole in the wall with a limited menu. They only make a certain amount of each item every day, so by the time we arrived around 2:00 p.m. they only had their Sicilian cheese pizza left. It was good, but we preferred the za we got at Regina Pizzeria. The crust and toppings at Regina were simply top notch. Beware, you will most likely need to wait in line for Regina but be patient. The two dessert spots we compared were Mike’s Pastry and Modern Pastry. Both were packed. Mike’s had more flavor options and more history, but Modern won over our taste buds because their custom cannoli are made fresh!
Galleria Umberto where they only have a certain amount of food each day.
The simple interior with a simple menu.
The only thing they had left by the time we arrived!
Pizzeria Regina, where there always seems to be a line.
Lots of options for pies here!
Mike’s Pastry
Higher rating for quantity.
Modern Pastry
Higher rating for quality.
Galleria Umberto where they only have a certain amount of food each day.
The simple interior with a simple menu.
The only thing they had left by the time we arrived!
Pizzeria Regina, where there always seems to be a line.
Lots of options for pies here!
Mike’s Pastry
Higher rating for quantity.
Modern Pastry
Higher rating for quality.
Charlestown
We followed the Freedom Trail brick line over the North Washington Street bridge to the Charlestown area. One of the Freedom Trail stops here is the Bunker Hill Monument which has 294 steps you can climb to snag some great views of the city! The other Freedom Trail stop is the USS Constitution (a.k.a. Old Ironsides). After going through security, you are able to tour almost the entire ship! We crouched our way through the boat which made us realize how much shorter people were back in the day! Instead of walking back over the bridge to downtown, we thought it’d be fun to go by boat, so we paid $3.70 to take the Boston Harbor Cruises ferry from the Charlestown Navy Yard to the Central Wharf. We sailed back while watching the sunset behind the Boston skyline as our night truly began.
Bunker Hill Monument in Charlestown.
We climbed the 294 steps to…
…a stellar view of Boston!
Boston Naval Shipyard
The USS Constitution
Hanging out on this ship from the 18th century!
Where the sailors slept!
Watching some boats be lifted out while waiting for the ferry.
The ferry we took back downtown.
Bunker Hill Monument in Charlestown.
We climbed the 294 steps to…
…a stellar view of Boston!
Boston Naval Shipyard
The USS Constitution
Hanging out on this ship from the 18th century!
Where the sailors slept!
Watching some boats be lifted out while waiting for the ferry.
The ferry we took back downtown.
Fort Point/South Boston
Once we arrived back downtown, we made a brisk walk down Seaport Blvd to Fort Point/South Boston. We would describe this port area as newer and a little more upscale with nice seafood restaurants. We made our way right to Trillium Brewing Company where there was surprisingly already a line to get in around 5:00 p.m. We enjoyed a variety of beers (mostly high ABV stouts and IPAs) here while we befriended some fellow Minnesotans!
Trillium Brewing Company
TD Garden
The main reason for our Boston day was for the Bruins-Wild game. So, we grabbed an Uber from Trillium up to the TD Garden for the 7:00 p.m. game! TD Garden is located in the West End and has some great bars in and around it! TD Garden is the venue for both the Celtics and the Bruins, and we must say there aren’t very many bad seats in the house. We bought the cheapest tickets we could find, and the players were much bigger than ants! Unfortunately, the outcome of the game wasn’t what we wanted, but it was fun to spend some time in this fantastic arena. The city has done a great job revamping it in recent years. We enjoyed our unique stadium dinner from the Frito-Lay Test Kitchen! One of the bars in the arena is Banners; we didn’t end up making it here, but we hear they have the largest TV in New England! Instead we walked a couple blocks to McGann’s Irish Pub where we reunited with the fellow Minnesotans we met at Trillium for a nightcap.
TD Garden
No terrible seats.
Go Wild!!!
Frito Lay Test Kitchen meals!
TD Garden
No terrible seats.
Go Wild!!!
Frito Lay Test Kitchen meals!
Castle Island
We didn’t visit Castle Island on this same day, but one of our first weekends in Massachusetts our amazing hosts took us to this area in South Boston. It’s connected to the mainland by a narrow strip of land now, so it’s not actually an island anymore, but the 2+ mile loop path is nice to walk around. You get to circumnavigate Fort Independence and you can catch some nice views of the Boston skyline if the lighting is right. Sullivan’s is the only food option in Castle Island which isn’t anything particularly special, but boy do they have tradition on their side! It is constantly packed as they have plenty of options to choose from for a pre/post-walk snack.
Fort Independence
Castle Island
Sullivan’s for a snack.
Fort Independence
Castle Island
Sullivan’s for a snack.
As you can tell, Boston has several different neighborhoods all offering something different. We probably won’t get to all of them, but it’s been fun to try!
