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Greetings Internet Stranger and welcome to 24 hours in Boston. When I say the phrase “24 hours in Boston”, people probably imagine tri-cornered hats, Paul Revere and his midnight ride, John F Kennedy, and the phrase “Paahk yah cah in Hahvahd Yahd.” And sure, you can find all of those things in Boston. But Boston has so much more to offer than colonial political history and hilarious accents.

Join me for 24 hours in Boston, and we’ll feast repeatedly on some of the finest Italian food in the country. We’ll walk along the Freedom Trail, and we’ll learn some secret and scandalous facts you never got in school. Finally, we will break into the Governor of Massachusetts’s office, and we will flee without getting arrested. Don’t believe me? You soon will.

24 Hours in Boston

Where to Stay?

It can be expensive to spend 24 hours in Boston, especially during the high seasons of summer and fall. I didn’t need to stay at the Ritz Carlton, but I wanted to find a hotel with a central location that wouldn’t steal all of my budget. That’s why I opted for the HI-Boston Hostel.

My room was giant and affordable (and despite the name “hostel”, it was a private room with a private bathroom). Plus the hotel was within walking distance of many major attractions in Boston like Boston Common and the Old State House. I think HI-Boston Hostel is the smart choice for a mid-range budget.

If you’re looking for a great deal on this hotel, click here. If you’d rather explore great deals on other hotels in Boston, click here.

24 Hours in Boston

What to Pack?

A Perfect 24 Hours in Boston 2

You’ll need comfy shoes for all the walking we’re going to do. If it’s summertime, I love my special pink Birkenstocks. These aren’t your grandpappy’s Birkenstocks anymore. They come in every shade, and I always get compliments on my electric magenta shoes.

A Perfect 24 Hours in Boston 3

If the weather is rainy or snowy, which happens quite often in New England, I recommend the Asgard Rain Boots. They are comfy/cozy and keep my feet dry all day. Plus they’re cute enough that I can wear them out without feeling like some gauche tourist with gross feet.

A Perfect 24 Hours in Boston 4

Finally, since we’re going to be out all day, you’ll want a battery for your cell phone. I always use the Anker charger. It’s light enough to fit in even a small purse. Plus the Anker lasts for several full charges of a phone, so I’ll never run out of juice!

24 hours in boston

24 Hours in Boston

Morning: North End Food Tour

Boston is so rich in history. The only other city in the northeast that can compare is Philadelphia. But it’s easy to get overwhelmed with all of that history and not even know where to start. That’s why I recommend booking a tour with a local in Boston to get your bearings. I used my favorite tour company Urban Adventures and their tour From Food to Freedom Trail, which lasted all morning and afternoon. I’ve used their tours from Tokyo to Detroit and I’ve never been disappointed.

The first part of the tour, which you can book separately, is the North End Food Tour. This tour will take you all around Boston’s legendary Italian neighborhood. I’m from New York City and I have to admit that the food in the North End is way better than the food in our Little Italy. I don’t want to spoil all the secrets of the food tour, but I’ll help you work up an appetite with…

approximately top 5: north end food tour

cheese fontina
1) italian pastries

Of course the right way to start your 24 hours in Boston in the North End is with an Italian pastry. We got ours at a hole in the wall called Bricco Panetteria. I never would have been able to find this spot on our own. Our guide, whom I shall call Sam Adams, recommended ordering a pastry stuffed with fontina cheese. I said yes because I never say no to cheese. It’s actually against my religion because we all know Blessed Are the Cheesemakers.

cappuccino boston north end
2) the cappuccino museum

Of course we all need to thank Italian-Americans for arguably their great contribution to world culture: the fancy coffee. I personally am a murderous goblin every morning until I’ve had my coffee, so I appreciate anything that makes great coffee easier to get and more delicious to drink. Sam Adams took us to an adorable Italian cafe that serves cappuccino with a light dusting of cocoa powder on top. Coffee + chocolate = morning happiness. That’s just science.

old cappuccino machines

But almost as cool as the makeshift mocha were all the old cappuccino and coffee machines sprinkled about the cafe. It was basically a cappuccino museum. And frankly, I think most museums would be a little more popular if the works of art could also make you a delicious beverage.

24 hours in boston pizza
3) pizza time!

As a native New Yorker, I am supposed to hate the pizza of all other cities. And yet I cannot bring myself to do this. Pizza is delicious, and you can get great pizza all around the world. (Bagels are a whole nother story, which will be told another time.)

Boston is not as famous for pizza as New York, Chicago, or St. Louis, but since there’s so much wonderful Italian food, of course you can grab a great slice. I highly recommend the place where we stopped, Galleria Umberto. The lines here get crazy long, so it was smart that we arrived just when it opened so we didn’t have to wait much. Just be aware that Umberto closes at 2:30. I cannot stress this enough: get here early!

Umberto is famous for its square slices and delicious crust. I detected a gracious note of cornmeal in mind. My favorite part of the pizza was how crusty the cheese got at the top. This was like the gourmet version of those Stouffer’s French bread pizzas I was obsessed with as a kid.

old north church
4) old north church

Of course, even a food tour in Boston needs to include some history. And the Old North Church is one of the most famous buildings in Boston. It was immortalized in Henry Wadsworth Longfellow’s poem “The Midnight Ride of Paul Revere”. The famous signal “One if by land, two if by sea”, was sent from the steeple of the church.

Of course, Longfellow took some liberties with the story. In the poem, Paul Revere was the person who received the Secret Lantern Message. But in reality, Revere helped send the message, not receive it. And there were many more Patriots involved in sending and receiving the message than there were in the poem. But Longfellow was trying to rally the North in the days before the Civil War, so all the changes were made to inspire patriotism during our country’s darkest period.

My favorite story about the Old North Church is about these angel statues. They look so sweet, but they are actually hot, and by hot I mean stolen. They were a gift to the church by a member named Thomas Gruchy. But the church was apparently unaware that Gruchy was a privateer who stole the angels from a French ship. Should we start a petition for the Old North Church to give them back to the French?

copp's hill burial ground
5) copp’s hill burying ground

Any crazy old city like Boston needs a place to bury its dead. And every cemetery in Boston is chock full of weird stories. Copp’s Hill Burying Ground has one of the oddest grave markers. The death date on the marker is 1625. But the cemetery didn’t exist back then. Spooky! It’s possible that the date is a prank, but it’s also possible that the corpse was originally buried elsewhere and then moved to Copp’s Hill Burying Ground. I choose to believe it was a prank, and the prankster was the ghost of Benjamin Franklin.

Franklin would have good reason to prank this particular burying ground because Cotton Mather was buried here. Mather was a Big Wig during the Salem Witch Trials. Young Ben Franklin, who grew up in Boston, did not approve of the Puritans and their hypocrisy. So as a teenager, he pretended to be a woman named Silence Dogood and wrote articles in his brother’s newspaper, some of which mocked Puritans like Mather.

(If you want to learn more about Franklin’s time in Boston, I recommend the podcast Young Ben Franklin, which was written by my very own father.)

mint chocolate ice cream
6) old school ice cream

Ice cream is always welcome, even in a freezing New England winter. But it’s much better to eat it in the summer. We stopped for a little old school Italian ice cream to finish off our tour. They didn’t have any crazy flavors, so I opted for my favorite, mint chocolate. Go with a simple classic flavor here, and you can’t go wrong.

24 hours in boston

24 Hours in Boston

Afternoon: Boston History and Highlights

Now that we were completely fed, it was time for the history portion of the tour. (You can book this tour separately as Boston History and Highlights.) This tour takes you to many of the major stops on the Freedom Trail. For those who haven’t spent 24 hours in Boston, the Freedom Trail is a literal red line painted on the streets that guides tourists past all the most historically important places in Boston.

It would be blatant highway robbery for me to spill all the secrets I learned with Sam Adams on the Boston History tour. But I’ll share some of my knowledge with…

three fun facts: 24 hours in boston

faneuil hall
1) what are the most famous places in boston?

The two most famous historical sights we saw on the tour were the impossible to spell Faneuil Hall and the Old State House. Faneuil Hall has been a gathering place for protests for about 250 years. It was originally built by a super rich dude named Peter Faneuil as a present for the city of Boston. The Sons of Liberty and Real Samuel Adams led many protests here, mostly about not wanting taxation without representation.

Nowadays, Faneuil Hall is a marketplace. But our guide, Fake Sam Adams, said that Faneuil Hall is still a meeting place for protests to this day. It’s a good thing that everything in America is going so well nowadays that no one has the need to protest anything!

old state house

The Old State House was the seat of the British Colonial government. The Boston Massacre took place here, which was one of the events that kicked off the American Revolution. Fake Sam Adams said that the horrors of the Boston Massacre were exaggerated by the Patriots because they wanted to rally Americans to the cause of independence.

In fact, the British didn’t mean to attack the protesting Americans. One of the British soldiers misheard his commanding officer and thought he was being given the order to fire. The first person to be killed during the Boston Massacre was a Patriot named Crispus Attucks, who was half African-American and half Native American. Abolitionists later honored Attucks as proof that African-Americans deserved equal citizenship.

old state house lion unicorn

One detail you might miss on the Old State House are these shiny animal statues. They were meant to represent the different nations that made up the United Kingdom during the colonial period. There was the lion for England, the unicorn for Scotland, and the eagle for America. I was tempted to ask “WHAT ABOUT WALES?” but I was worried the tour guide would find this question obnoxious. And we’re not spending 24 hours in Swansea.

uncle tom's cabin boston
2) what about lesser known sights?

Internet Stranger, I give you…this historic Chipotle! It used to be a printing press where the landmark blockbuster Uncle Tom’s Cabin was published. Abolitionist Harriet Beecher Stowe wrote this book to show the horrors of slavery. Many people credited her with changing public opinion in the North so that more believed it was worth going to war to end slavery. When Abraham Lincoln met her, he even said, “So you’re the little woman who wrote the book that started this great war.” Never underestimate the power of a woman with a pen!

irish memorial

We’ve talked all morning about the Italian community in Boston, but let’s not forget the Irish! After all, the most famous family to come out of Boston are the Irish With a Capital Oi Kennedys. This memorial shows the progression of Irish-American history in Boston. The first Irish people arrive starving, barefoot, and in rags. They were escaping the famine and potato blight in their home country. Then we can see the next generation of Irish-Americans, strong, upright, and well dressed.

I suppose if the memorial were honest, the next generation of Irish-Americans should be bootlegging, winning shady political elections, and cozying up to Marilyn Monroe? That is the American Dream, after all. (I’m Irish-American myself, so I kid with love.)

gould shaw memorial boston

My favorite memorial in Boston is the one to Robert Gould Shaw and the Massachusetts 54th. Gould Shaw was a white abolitionist in his mid-20s who was selected to lead the Massachusetts 54th regiment, the first all black regiment in the Northeast, during the Civil War. Shaw and his men showed remarkable courage under difficult circumstances. Shaw was angered that the black soldiers weren’t paid as much as the white soldiers and helped the regiment fight for equal pay.

The Massachusetts 54th was sent to a virtual suicide mission when they led the assault on Fort Wagner in South Carolina, and Shaw and many of his men were killed. But their courage is still remembered, especially by anyone who has seen Denzel Washington’s Oscar winning performance in Glory. If you haven’t, stop reading this blog immediately and go watch it.

boston state house
3) is there any history still happening in boston?

First of all, why are you still here when I told you to go watch Glory? If you are still reading, I assume that you’ve finished watching the movie, so I’ll answer your question. Yes, Boston is the capital of Massachusetts, so history happens at the State House every day. I always forget Boston is the capital because in so many states, the biggest city isn’t the capital. In my home state of New York, the capital is Albany, or as I like to call it, Pure Trash.

govenor of massachusetts balcony

The most famous person in the Massachusetts State House is the governor. Currently the governor is Charlie Baker. He manages to be an extremely popular governor even though he is a Republican and Massachusetts is an extremely left-wing state. In the State House you can see the portraits of previous governors of Mass. Some of the most famous are John Hancock, whose giant signature is on the Declaration of Independence, and Mitt Romney, the now Junior Senator from Utah.

I probably shouldn’t tell you this because I can’t guarantee it will happen on every tour, but we actually got to go on the governor’s private balcony. That’s where I took the photo above. The governor was not in and Fake Sam Adams seemed to be friends with his secretary, so that’s how we got in. I felt like Silence Dogood, spying on the whole city!

boston public garden

24 Hours in Boston

Late Afternoon: Boston Public Garden

I’m a big believer that people should spend the late afternoon of a perfect 24 hour itinerary relaxing and recharging their batteries. And now is the time in your 24 hours in Boston when you’ll need a break. On a beautiful summer day, there’s no better place in Boston to do that than Boston Public Garden. It’s the oldest botanical garden in America because every single damn thing in Boston is the oldest in America.

Sit back and relax with a book, ride on a swan boat, take this free walking tour of notable trees…you do you!

24 hours in boston public garden
24 hour treasure

My favorite spot in Boston Public Garden is the statue of the ducklings in Robert McCloskey’s famous Boston-set children’s book Make Way for Ducklings. Look how cute the baby ducklings are in their little scarves. Also Robert McCloskey is a distant cousin on my Irish-American mother’s side. That’s the second family member I’ve promoted in this blog post! Woo hoo for nepotism! I’m a true Bostonian now!

caesar salad

24 Hours in Boston

Evening: Dinner at Strega

I didn’t know where to eat dinner that evening, so Fake Sam Adams suggested I dine at Strega, an upscale Italian restaurant on the Waterfront. (There’s another Strega in the North End, but it’s harder to get into last minute.)

They serve classics but with a twist you won’t find at many red sauce joints. So you can get a Caesar salad, but it was made with top quality cheese and very lightly dressed, so the lettuce wasn’t drowning in gloop like it does in a mediocre Caesar. (Mediocre Caesar was Julius’s little-known cousin.)

rigatoni all vodka

For the main course, I recommend the rigatoni with vodka. The menu told me this was a favorite of the Boston Celtics. So basically eating this is like dining with Larry Bird. As with the Caesar, the rigatoni wasn’t overdressed, so you could really get the flavors of the spicy sausage.

strega boston cannoli

For dessert, I had my very favorite dessert ever, the cannoli. I grew up near Little Italy, so my mom would always take me to an Italian bakery for cannoli if I earned a special treat. Now every time I bite into a cannoli, it’s like I’m eating my dead mother’s love. But if you eat the cannoli at Strega, probably all you will taste is a crunchy pastry shell filled with luscious sweet ricotta. Close enough!

24 hours in boston

That’s a Perfect 24 Hours in Boston!

What would you do with 24 hours in Boston? How many more family members can I promote in this blog post? And is it okay to make fun of Kennedy, or is it still too soon? Please leave your thoughts below!

Note: If you want to know how I put my travel itineraries together, just click here. Keep in mind that while each article is about how to spend 24 hours in a place, that doesn’t mean you should ONLY spend 24 hours in Boston. If you have time for another 24 hours in Boston, try this itinerary.

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