Best Historical Tours in Boston 2023

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Greetings, Internet Stranger, and welcome to the best historical tours in Boston! Boston, Massachusetts is a city with a rich history and many fascinating gems to explore. That’s why one of the best things to do in Beantown is check out one of the best historical tours in Boston.

I’ve been going to Boston since I was eight years old, and I love its history just as much as anybody. That’s why I’m happy to share with you the best historical tours in Boston, and yes, I promise I’ve really been on all of them!

Best Historical Tours in Boston

1) North End Food and History Tour

Boston is incredibly rich in historical goodies. In fact, I would say that the only other American city that has nearly as much history Philadelphia. In fact, there’s so much history in Boston, it’s hard to know where to begin. That’s why I recommend booking one of the best historical tours in Boston with a local to find out all the most important places.

I strongly suggest the wonderful North End food tour.

Check rates and availability by going here.

Food tours are the best way to get to know a city’s secrets and fun historical facts. And it’s even better when a food tour is one of the best historical tours in Boston.

The North End is one of the most historically important neighborhoods in the city. Plus, it’s Boston’s Little Italy, so the food is amazing! You really can’t go wrong here.

Check rates and availability of this tour for yourself by clicking here.

Of course the right way to start one of the best historical tours in Boston in the North End is with an Italian pastry. If you want to know all the best secret places that have been serving pastries for years, join in on this food tour and you will learn them all.

Our guide, whom I shall call Sam Adams, suggested that we order a pastry stuffed with fontina cheese. I personally think that cheese is the best way to start any breakfast, or lunch, or dinner, so you can’t go wrong with this suggestion.

One reason that Italian Americans have been historically important to the American food scene is that they brought proper coffee to the United States. I’m used to going to old Italian coffee joints in my hometown New York City, but the ones in Boston are just as good and historically important.

Sam Adams took us to an adorable Italian cafe that serves cappuccino with a light dusting of cocoa powder on top. The only thing better than coffee in the morning is coffee and chocolate in the morning. Everyone knows that.

And if you’re interested in coffee, you’ll love the old coffee and cappuccino machines in the cafe. It was basically a cappuccino museum, which definitely makes this one of the historical tours in Boston. I think more people would like museums if they also served you delicious coffee.

Some people think that New Yorkers only like pizza in New York City. Well, I can tell you that this is a total lie. I’ve enjoyed pizza everywhere from Milwaukee, Wisconsin to Albuquerque, New Mexico.

I don’t know that Boston is exactly a famous pizza city, but they do have so many wonderful Italian restaurants, so you know their pizza is delicious!

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 this place closes fairly early in the day. I cannot stress this enough: get here as soon as you are able.

This pizza is famous for its scrumptious cornmeal crust, and I say this as someone who usually doesn’t finish her crusts. This time, I ate all of mine!

I told you that this was one of the best historical tours in Boston, didn’t I? Well, that means that it’s time for some history. And the Old North Church is one of the most famous historical buildings in Boston. It was made famous in Henry Wadsworth Longfellow’s poem “The Midnight Ride of Paul Revere”. If you’ve heard of one if by land, two if by sea, that happened at this church.

Of course, Longfellow took some liberties with the story. In the poem, Paul Revere was the person who got the Secret Lantern Message and spread the news far and wide. But in real life, Revere sent the message, he did 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 its 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?

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, so you know it’s historically important. 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. He did love a practical joke.

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. Again, he was basically Prank Sinatra.

Ice cream is always welcome, even in a freezing Boston winter. However, I think it’s much better to eat it in the summer. We stopped for some classic 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 Hour Tip

There’s lots more hidden tricks and treasures you can find on this fine example of one of the best historical tours in Boston.

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2) Boston History and Highlights

If you’re a true history buff you’ll love the Boston History and Highlights tour. It’s definitely one of the best historical tours in Boston.

This tour takes you to many of the major stops on the Freedom Trail. For those who aren’t familiar with the best historical tours 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. If you’re a history buff, you simply must come here.

Check rates and availability of this tour right here.

It would be so wrong for me to spill all the historical fun facts that I learned with Sam Adams on one of the best historical tours in Boston. However, I’ll be glad to share my favorite info.

The two most famous historical sights we saw on the tour were the really hard to spell Faneuil Hall and the Old State House, which is easier to spell. Faneuil Hall has been a popular magnet for protests for over two centuries years. It was originally built by an unfathomably wealthy gent named Peter Faneuil. He donated it as a present for the city of Boston.

Famous patriot groups in the American Revolution, including actual Samuel Adams, not my tour guide, led many protests here, mostly about not wanting taxation without representation.

Nowadays, Faneuil Hall is just used for selling goods, at least officially. However, Fake Sam Adams said that there are still many protests here to this day. Gosh, I wonder what people in the United States have to be upset about!

Up here we can see the Old State House, which is where the Boston Massacre took place. That’s why one of the best historical tours in Boston has to stop here. Sam Adams said that this attack, though deadly, wasn’t really a massacre. The Patriots just wanted to get public opinion on their side.

The British didn’t mean to attack the protesting Americans at all, really. One of the British soldiers just misheard his commanding officer’s order.

The first person to be killed during the Boston Massacre was an African-American patriot named Crispus Attucks. Abolitionists in Boston used his name a lot to prove that slavery was an immoral institution.

Look up when you get to the Old State House, so you can see these metallic animal statues. They represent different parts of the British Empire. The lion is for England, the Unicorn is for Scotland, and the eagle is for the US of A. I asked where Wales was, but no one would tell me.

I told you that we’d see many wonders on the best historical tours in Boston. But did you think we’d see a historic Chipotle? It used to be a publisher whose most famous book was the abolitionist classic Uncle Tom’s Cabin.

Some people even credited her with changing public opinion about slavery so much that it led to the Civil War. If you’ve never read Uncle Tom’s Cabin and you’re interested in history, I suggest doing so. It’s old fashioned, but it’s an important part of American history.

Here we have a monument honoring the Irish American community in Boston. Obviously, the most well known Irish Americans in Boston are the Kennedy family, or possibly the Afflecks.

This memorial honors the first Irish immigrants who came to escape the great famine back home. (I’m Irish on my mother’s side, and our family did the same thing, but we came to New Orleans.) However, the memorial also shows how the Irish prospered after they came to the United States.

It doesn’t show the Irish causing the Cuban Missile Crisis and having an affair with Marilyn Monroe, though. I know because I asked.

You can’t take a historical tour in Boston without seeing the famous Robert Gould Shaw Memorial. It is dedicated to Shaw and the regiment he led during the Civil War, the famous Massachusetts 54th. This was the first all Black American regiment in the Northeast during the Civil War.

Shaw and his men were extremely brave, and they fought for equal pay for Black soldiers. (Those of us in the North sometimes like to think that the racism was all in the South, though of course this wasn’t true.)

The Massachusetts 54th was sent on an extremely dangerous suicide mission when they led the assault on Fort Wagner in South Carolina. Fort Wagner doesn’t exist anymore, but you can see where it was if you visit Fort Sumter in Charleston.

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 as a fictional member of the regiment. If you haven’t, stop reading this post immediately and check it out.

First of all, why are you still here when I told you to go watch Glory? We’ll I will give you the benefit of the doubt and assume that you have seen the movie, so we can keep going about Boston. Boston is the capital of Massachusetts, so it’s appropriate for a historical tour to stop at the State House every day.

I always forget Boston is the capital of Mass, because in so many states, like Illinois or Pennsylvania, 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, EW. (Just kidding Albany! You actually have some decent Thai food.)

The most famous person in the Massachusetts State House is the governor. Currently the governor is Maura Healey, but the governor when I took this tour was Charlie Baker. He managed 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 to you when you take the tour, but we actually got to peek out on the governor’s private balcony, 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 can’t guarantee Sam Adams is friends with the new governor though!

24 Hour Tip

There’s lots more hidden history of Boston for you to enjoy on this amazing version of one of the best historical tours in Boston.

Go ahead and check out the tour by going over here to try it for yourself!

3) Secret Food and History Tour

Again, the only thing better than the best historical tours in Boston is taking a fabulous history and food tour in Boston. And I promise that this tour is definitely one of the best.

We spent some time exploring history in the North End, but we also got to learn more about modern Boston at the Boston Public Market. Plus there was lobster! What more can you want on a fabulous historical tour!

Check rates and availability for yourself by clicking here.

I don’t want to spoil the whole tour, but I do want to get you excited to take the tour yourself!

This one of the best historical tours in Boston began in the famous North End of Boston, which I mentioned is Boston’s Little Italy. And what’s a Little Italy without some amazing pizza to devour?

Our guide, whom I shall nickname Isabella, said that Boston doesn’t really have its own pizza style. That’s one thing that makes Boston pizza eating so fun! You can get anything here from a classic New York-ish slice to a satisfying circle style pizza like the one you see in my little photo.

One thing that makes this food tour special is that every tour has a Secret Dish that is only revealed on the day of the tour. We had our secret bite at the same restaurant as the pizza, which was nice as it meant sitting for a longer period of time. All I can say is that it’s a type of pasta and that it involved a GOURD. Again, this is all I can say.

Another feature of most of these food tours is that you can get an optional drink package. For this food and history tour, that meant getting a glass of Chianti with my pizza and pasta. Why wouldn’t you want the extra Chianti, as my grandmother used to say.

Italian-Americans rightfully get lots of positive press for their pizza, pasta, and ice cream. But let’s not forget that they are also amazing sandwich makers, which is why you should try a muffaletta. I was surprised to see a muffuletta sandwich on this tour because I had thought you could only get them in New Orleans.

It seems I was deeply wrong, and any Little Italy can have a muffaletta. A muffaletta features a perky olive salad on a meat and cheese sandwich. It requires a thick roll because the olive oil soaks into the roll and makes it flawless.

Isabella started telling us some of the fascinating history behind the North End. My favorite story was about the Sacco and Vanzetti Defense Committee, which operated in the North End during the 1920s. Sacco and Vanzetti were two Italian-American anarchists who were convicted and executed for an armed robbery/murder.

Nowadays the trial is believed to be a serious injustice, as Nicola Sacco and Bartolomeo Vanzetti didn’t even understand everything that was happening at trial because they couldn’t speak English fluently.

It’s widely accepted that Sacco and Vanzetti didn’t commit the murder, but no one will tell me who did. It seems that we have a history mystery on our hands.

At this point on our food and history tour we left the North End and headed for the Boston Public Market. This market is historically important because unlike many other markets in this world, all the vendors have to be Bostonian.

Our first stop was at the Boston Honey Company to try many delicious kinds of local honey. The clerk said that you want to eat as much honey as you can from your own neighborhood because it will help you with allergies. It’s something to do with pollen but I am not sure exactly what because I am not a bee scientist.

I’m sure you’ll enjoying many of the most wonderful honeys in Boston. Who knew Boston could be so sweet? Now, some of you are probably thinking about where bees go in Boston winters. After all, it gets so cold, how can the bees keep making honey?

The clerk told us that they send their bees to Georgia when the weather gets cold. In the Peach State it is so warm year-round that if even one half-inch of snow falls, the entire city of Atlanta is paralyzed. Smart thinking, bees!

Our next stop was at a nut store for Boston’s finest nuts. I hope you’re not thinking that I would stoop to making a naughty joke about nuts, and I assure you that a naughty joke has never even once crossed my mind.

This tasting was at an adorable little nut shack where we got to try almost ten different kinds of nuts. I never knew nuts could come in so many flavors. We tried it all, from chocolate to bourbon to hot pepper.

The chocolate was the most popular flavor, but I enjoyed them all. If you or a loved one enjoys heat, don’t miss the hot pepper nuts. In general, nuts are a pretty healthy snack.

As with the Boston Honey Company, you get a discount with anything you buy, just for being on the tour. But no one was giving the hard sell to buy anything, so no worries.

You can’t have a food and history tour in Boston without lobster. Some might call it lobstah because that’s the way it sounds with a Boston accent. Our guide had a pretty strong Boston accent, so we enjoyed hearing her say lobstah many times.

We got these lobster rolls at a fantastic stand called Red’s Best. The fish is so fresh they can actually tell you the name of the boat that caught each fish. My favorite thing about the roll is that the lobster wasn’t overdressed at all. When you have lobstah that’s this wicked awesome, you don’t want to cover up its flavah with a lot of mayonnaise. 

There are many reasons to like Boston, even if you detest the Red Sox and the Patriots as many very intelligent people do. However, I think the best reason to come is the famous cannoli of Boston. Cannoli are my very favorite dessert and I eat them every birthday. I sometimes fantasize about changing the name of this blog to Around the World in 24 Cannoli.

Mike’s Pastry has the most well known cannoli in Boston, but Isabella took us to a different shop, which she says is better. The cannoli are filled to order and they tasted like ricotta made from the laughter of God’s most wicked awesome angel. As is only proper, our cannoli were paired with a frothy cappuccino. The perfect end to a perfect tour.

24 Hour Tip

That’s all the food we ate, but if you want to actually eat the food yourself and learn all the secrets I didn’t share…

just go ahead and book the tour by clicking here.

Best historical tours in Boston

Where to Stay?

It can be expensive to spend a day with the best historical tours in Boston especially during the high seasons of summer and fall when the leaf peeping is on. I didn’t need to stay at the fanciest spot, but I wanted to find a hotel with a central location that wouldn’t steal all of my budget. That’s why I suggest staying at the Moxy Boston Downtown.

The rooms are giant and affordable and comfortable. Plus the hotel is within walking distance of many major attractions in Boston like Boston Common and the Old State House. I think this hotel is the smart choice for any guest in Boston.

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.

This search engine will help you find the most affordable and convenient hotel during your day of the best historical tours in Boston. With hundreds of options to choose from, I’m sure you’ll find something for your schedule and budget.

Best historical tours in Boston

Shopping List

• An excellent small cell charger so you can keep taking pictures of your best historical tours in Boston
• My favorite guide to New England, including Boston
• These great TSA approved clear toiletries bags, so I can always keep spare toothpaste and travel sized toiletries in any carry-on
• The most reliable travel umbrella that is small enough to fit in my purse, but strong enough to stand up to powerful winds during our day of the best historical tours in Boston
• My book Get Lost, that I wrote myself with all my best travel tips. This book will show you how travel can take you on a journey of self-discovery.

That’s the best historical tours in Boston!

What do you think are the best historical tours in Boston? Email me at stellajane@aroundtheworldin24hours.com and let me know!

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 have a day of the best historical tours in Boston.

Add on a day of the best Mystic Seaport things to do. Find the best things to do in Mystic CT. You can try 24 hours in Providence. Let’s go for the top things to do in Providence RI. Get to know the best Boston places to visit. You can also try 24 hours in Boston.