A Perfect One Day in Boston Itinerary

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Greetings Internet Stranger and welcome to a one day in Boston itinerary. Everyone knows Boston is famous for its Freedom Trail and American Revolution-era attractions. But Boston is not completely stuck in the 18th century, as you’ll learn on this One Day in Boston Itinerary! There are more modern attractions like the Isabella Stewart Gardner Museum and the Boston Public Market. Plus there’s a fine dining scene you won’t want to miss out on!

Join me for a One Day in Boston Itinerary, and we’ll see the side of the city that tour guides wearing tri-cornered hats and breeches never get to visit. (Not that there’s anything wrong with silly hats and breeches! You do you, Tour Guides of Boston!)

One Day in Boston Itinerary

Where to Stay?

It can be expensive to spend a One Day in Boston Itinerary, 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. And it’s easy to get to the Isabella Stewart Gardner Museum from here by subway. 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.

One Day in Boston Itinerary

What to Pack?

A Perfect One Day in Boston Itinerary 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 One Day in Boston Itinerary 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 One Day in Boston Itinerary 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!

One Day in Boston Itinerary

One Day in Boston Itinerary

Morning: Secret Food Tour

Some of you might be noticing that we did a food tour in the morning during our last One Day in Boston Itinerary. Why are we doing another one today? Well that just proves how great the food scene has become in Boston, that we can do two consecutive food tours and not have any overlap.

I am a big fan of the company Secret Food Tours. They operate in many cities around the world, and their tours always take me to places I wouldn’t have found on my own. So I was excited to see that they operate a Secret Food Tour in Boston. We spent some time noshing on Italian treats in the North End, but we also got to more modern tastes at the Boston Public Market. Plus there was lobster! What more can you want?

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

approximately top 5: secret food tour boston

north end boston pizza
1) pizza pie!

The One Day in Boston Itinerary began in the famous North End of Boston, aka Boston’s Little Italy. And what’s an Italian-American neighborhood without some amazing pizza to chow down on? Our guide, whom I shall nickname Isabella, said that Boston doesn’t really have its own pizza style. You can get anything here from a classic New York-ish slice to a satisfying circle style pizza like the one you see above. The crust looks thick in the photo, but it was actually quite thin.

One thing that makes Secret Food Tours 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. I cannot reveal to you the exact nature of the Secret Bite, no matter how much you beg and cry. All I can say is that it’s a type of pasta.

Another feature of most Secret Food Tours is that you can get an optional drink package. For the Boston Secret Food Tour, that meant getting a glass of Chianti with my pizza and pasta. I always go for the optional drink package because wine makes everything better. That’s just science!

muffuletta Boston
2) muffuletta

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. I was surprised to see a muffuletta sandwich in Boston because I thought they were exclusively a New Orleans thing! But apparently you can find muffulettas anywhere you find Italians. Muffuletta refers to the sassy olive salad on a meat and cheese sandwich. You need a thick roll because the olive oil soaks into the roll and makes it extra-amazing.

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 grave injustice, as Nicola Sacco and Bartolomeo Vanzetti didn’t even understand everything that was happening at trial because they were not fluent in English.

It’s widely accepted that Sacco and Vanzetti didn’t commit the murder, but then who did? Why hasn’t this historical mystery been solved? Get on it, mystery writers of the world! All I ask is that you pay me ten percent of the gross of the sales of the book.

sweet honey boston public market
3) honey do be mine

At this point in the tour, we left the North End and headed for the Boston Public Market. This market is special because unlike many other markets in Boston, all the vendors have to be local. Our first stop was at the Boston Honey Company for samples of different types of honey. You want to keep it local for honey because eating local honey is great for relieving allergies. You built up a tolerance for the pollen all around you.

I had a sweet time sampling the different honeys and noticing how each one tastes different depending on the plant the bee that produced it was making sweet love to at the time. Some of you might bee wondering where the Boston bees go during the winter. Wouldn’t it bee cruel to force the bees to suffer through a frigid New England blizzard?

Apparently these bees like to winter in Georgia, where it is so warm year-round that if even one half-inch of snow falls, the entire city of Atlanta shuts down. Well played, bees!

qs nuts
4) qs nuts

Some of my readers out there might be hoping I will make some naughty jokes about nut sampling. I assure you I will do no such thing! I am a classy, classy lady who just happens to like nibbling on nuts from time to time.

This tasting was at a flavorful nut shop called Qs Nuts. Here we snacked on about eight different nuts and we didn’t even come close to trying them all. There was everything from bourbon to chocolate to hot pepper to savory nuts like rosemary. The chocolate was the biggest hit, but I didn’t meet a nut I didn’t like. The shopkeeper at Qs Nuts said none of them were fried so they would be healthy. I still don’t think it’s very healthy to be popping nuts in your mouth all the time, but you do you, Internet Stranger!

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. (Most of us on the tour did buy nuts and honey, perhaps so we could make our own bootleg Honey Nut Cheerios.)

boston public market lobster
5) lobstah!!!

I call it lobstah because that’s the way it sounds with a Boston accent. I thoroughly embarrassed Isabella by asking her to say the word supermarket for me. (Supermahhhhket!) Sometimes I am a very mean person.

But back to the lobstah. We got these lobster rolls at a stand called Red’s Best. The fish is so fresh they sometimes put the name of the boat the fish was caught on next to the fish they are selling. I liked how the lobster wasn’t overdressed at all. When you have lobster this wicked awesome, you don’t want to cover up its exquisite flavor with a lot of mayonnaise. 

6) cannoli

There are many reasons to like Boston, Mass, even if, like all right thinking peoples, you hate the Red Sox and the Patriots. But the one that keeps me coming back is the wondermous cannoli of Boston. These are my very favorite dessert of all time. I sometimes fantasize about changing the name of this blog to Around the World in 24 Cannoli.

Mike’s Pastry has the most famous cannoli in Boston, but Isabella took us to Modern Pastry, which she says is better. The cannoli are filled fresh and they tasted like ricotta that died, went to heaven, and then was beatified by the Pope. As is only proper, our cannoli were paired with a frothy cappuccino. We’ll need the energy from the caffeine after all that food. We’re about to head to the most beautiful spot in Boston!

Isabella Stewart Gardner Museum

One Day in Boston Itinerary

Afternoon: Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is my favorite place in Boston. In fact, The Isabella Stewart Gardner Museum is one of my places in the entire world. My dream in life is to decorate my home so it resembles the The Isabella Stewart Gardner Museum. If the only thing in Boston were The Isabella Stewart Gardner Museum, it would still be worth visiting. I could go on. Safe to say, no One Day in Boston Itinerary is complete without stopping here.

Now that I’ve successfully injected enough hyperbole into the situation, I hope I’ve piqued your curiosity about this magical place. What makes the The Isabella Stewart Gardner Museum so special is that it is located in the actual home of the late Mme. Gardner, who was a formidable personality.

Isabella dedicated her whole life to learning and the arts, and when she died, she wanted her home to become a museum. You can find out more about the Isabella Stewart Gardner Museum on their website. One fun fact is that if your name is Isabella, you can get into the museum for free. Of course I have much more than that little tidbit to share with you…

three fun facts: isabella stewart gardner museum

Isabella Stewart Gardner Museum
1) so who curated the museum?

Why, Isabella Stewart Gardner herself! She was an extravagantly wealthy lady, and all she wanted to spend her wealth on was beautiful things. Truly she was a woman after my own heart. I’m so sad that she died before I was born so we can never be friends. I would even be friends with her ghost, no questions asked.

Isabella put all the objects in the Isabella Stewart Gardner Museum next to other objects she thought would suit them. Often these are objects from the same time period and country, but not always. And sometimes you have to think a little about the connection between different objects in the room.

Isabella Stewart Gardner Museum baby jesus

For example, look at how this painting above emphasizes the baby Jesus’ foot…

Isabella Stewart Gardner Museum foot

And then notice this sculpture of a foot nearby! So clever! Truly Isabella Stewart Gardner was the mad genius of Boston. When you visit, take your time trying to notice as many of these little messages from Isabella as you can.

Isabella Stewart Gardner Museum empty frames
2) what’s with the empty frames?

No, those paintings aren’t being taken to be cleaned, Internet Stranger! They are the result of a Major Art Heist that happened at the Isabella Stewart Gardner Museum in 1990. The artists who got heisted include Rembrandt, Degas, Manet, and Vermeer. I get that people steal art to sell it and make money. But what kind of lunatic would spend all that cash on a Rembrandt that they could never show to anyone. Did Thomas Crowne pull off the Isabella Stewart Gardner Museum heist?

As you’ve probably guessed by now, the thief/thieves have never been found and are still wanted by the FBI. The Isabella Stewart Gardner Museum offers a 10 million dollar reward to anyone who can locate the paintings. I’m pretty sure I know who took the paintings: it’s the same person who committed the Sacco and Vanzetti murder. I’ll take my reward in cash, please and thank you.

Isabella Stewart Gardner Museum garden
3) what’s the best day to have your One Day in Boston Itinerary here?

That’s clearly Thursday, when the museum stays open until 9. That should give you plenty of time to explore every nook, cranny, and oddment in the museum. You’re even luckier if you visit on the Third Thursday of a month. Then it’s party time at the Isabella Stewart Gardner Museum.

Isabella Stewart Gardner Museum puppy

Each Third Thursday has its own theme. When I was there, it was Puppy Evening or something and we all got to frolic with emotional support puppies on the lawn. A great time was had by all, especially the puppies. Puppies really know how to live.

Isabella Stewart Gardner Museum champagne

Even if you’re not into puppies, you monster, you can get into the free live music and the not-free live booze. Sip on a Bellini and chillax in the most beautiful spot in the museum, the courtyard/garden. Try to act really cool so that Isabella Stewart Gardner’s ghost will want to be your friend. The plants in the garden change nine times a year, depending on the season. Look closely and you’ll notice that all the artwork in the courtyard depicts women. Well played once again, Isabella!

One Day in Boston Itinerary

Evening: Dinner at O Ya

Boston hasn’t always been known for its fine dining. You’re historically more likely to go there for cannoli or clam chowdah. But that’s changing all the time, and dining doesn’t get any finer than the Japanese restaurant O Ya. (Or more expensive, this is definitely a special occasion restaurant. But it’s worth every penny.)

Since you’re breaking the bank anyway, end your One Day in Boston Itinerary right with the 18-course omakase tasting menu. You won’t be able to choose what you get, but you will be able to feast on the finest dishes available that evening. The beverage pairing is also excellent, but be prepared because it’s a lot of booze. You don’t want to slide off your chair like I did at the end of the evening. Don’t feel pressured to finish it all.

I am not going to walk you through all 18 dishes because as charming as I am, I think you’d be asleep by the time I was done explaining. Instead, I’ll limit myself to…

approximately top 10: o ya

o ya boston
course one

This baby is a Kumamoto oyster with watermelon pearls and cucumber mignonette. It was as refreshing as a blizzard on a typical March day in Boston. Also for some reason I wrote in my notes “don’t forget to chew the oyster”, and I have no idea why I thought this was important to say. I wasn’t even drunk yet at this point in the meal!

o ya boston
course two

Up next is cobia with banana pepper on top. This dish kicked like a Red Sox fan in a down and dirty brawl with a Yankees partisan. I liked the novelty of having a spicy piece of sushi that didn’t use any wasabi.

o ya boston
course three

This little bite was probably the most indulgent on the menu. It’s Hokkaido sea urchin with Osetra caviar. The uni tasted as rich as a Kennedy who got married to a Kerry.

mackerel o ya boston
course four

There’s no cocaine in this dish. That would be too decadent, even for O Ya. It’s actually local mackerel with vinegar powder on top. I loved the sour taste of the vinegar powder, but eating vinegar this way is as surprising as finding out that Ben Affleck was secretly behind the Isabella Stewart Gardner Museum heist.

o ya boston
course five

This ordinary looking roll is actually made with toro, fatty tuna, and wagyu chicharron. Chicharron are basically pork rinds, so you know you’re dealing with decadence when you’re eating chicharron made from wagyu.

I loved the flavors of this dish, but the roll fell apart when I bit it. I was as sad as Boston will be when Tom Brady finally retires.

chicken truffle mushroom
course six

This confusing-looking sushi above was actually made with Chicken of the Woods mushroom. But the mushroom was so umami, you could have fooled me into thinking I was eating real chicken. It was as deceptive as a woman in a Dennis Lehane novel.

foie gras powder
course seven

This unassuming spoonful is actually stuffed with foie gras powder. Apparently Fancy Powders That Are Definitely Not Cocaine is a theme at O Ya. My waiter told me to put the entire spoon in my mouth at once, and I was tempted to tell him to not tell me what to do. I was as cranky as a Bostonian when he arrives at a Dunkin Donuts for his morning coffee and finds it’s been shuttered by the Board of Health.

o ya boston
course eight

This surprising dish was spinach and caviar served with plankton butter. I had never eaten plankton before. I always just thought of them as the teeny creatures that whales eat, and did not realize humans could partake as well. It’s very rich and salty with all the butter and caviar, so the bitter spinach was the perfect touch.

I apologize for the quality of this photo. At this point in the evening, I was as drunk as Ted Kennedy’s ghost. (But still less drunk than Actual Ted Kennedy.)

o ya boston
course nine

Yup! The blurry quality of this photo tells me I am still drunk! This is chawanmushi, a savory Japanese egg custard. You can mix pretty much any savory item into chawanmushi if you are so inclined. O Ya went for broke with even more foie gras and crispy chicken skin. Look at all the foie gras and caviar I was getting this evening! I was as satisfied as Sully and Denise during a public make-out session.

o ya boston
course ten

Our last savory dish of the night is…even more foie gras! What is the New York branch of O Ya even going to do when the foie gras ban goes into effect. This is foie gras sushi topped with balsamic chocolate sauce, so it tasted almost like dessert. And I’d almost rather have foie gras than dessert, especially as sweets are not the specialty of most Japanese restaurants. I was now ready to roll my way home, as happy as the fans of all non-Patriots sports teams will be when Tom Brady finally retires.

That’s a Perfect One Day in Boston Itinerary!

What would you do on a One Day in Boston Itinerary? Have I really solved the museum heist? And what’s worse than Boston sports teams? (The answer is nothing.) 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 have a One Day in Boston Itinerary. If you have time for another One Day in Boston Itinerary, try this one!

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