In September of 2014 a friend of mine, born and raised in Massachusetts, called me up and said “We’re going to Boston”.
I said; “If you’re my tour guide you’re damn right we’re going”.
It was that simple.
We were headed to Boston.

In addition to this friend of mine being a total Foodie he’s also a Chef.
So we made it a point that the #1 thing we were going to do in Boston was EAT.
And eat like we’d never eat again.

When people hear about pizza in the United States they always think of New York.
There’s no doubt in my mind that NY has unbelievable pizza.
Yet I’ve learned there’s no way someone can deny the amazing Boston pizza that comes out of Massachusetts.

We took a red eye flight from Phoenix to Boston, so we arrived just as the sun was coming up.
After finding our B&B we immediately headed towards the North End(Little Italy).
Before we dove headfirst into Italy we had to stop at a place just opposite of the North End.
Located right around the Irish Pubs near Haymarket, is the appropriately named Haymarket Pizza(106 Blackstone St.).


I’d consider this place a bit of a hidden treasure.
It’s definitely a little hole in the wall type of place and your “table” is usually a piece of plywood laid over 2 seesaws.
Nothing fancy here, just a place to grab an enjoyable slice of pizza.
The pizza slices only range from $1-$3 depending on the slice you want.
It’s definitely worth stopping by just for the price alone.
They specialize in thin crust pizzas and have quite a bit of variety as far as toppings go.
I had two different slices(Chicken and Cheese) and they were both just as good as the other.

Chicken Pizza from Haymarket Pizza.
Chicken Pizza from Haymarket Pizza.

Once we left there we wasted no time crossing over the street into the North End.
If you love Italian food, this is the place to be in Boston.
The North End, which is only 0.36 square miles(0.93 km2), has over 80 restaurants throughout their cobblestoned streets.


We made our way to one of the most famous pizzerias in Boston, known as Galleria Umberto(289 Hanover St.).
This is a No Fuckin’ Around Type Of Place.
They make 1 style of pizza, Sicilian style.
You get Dough and you get Cheese. Enjoy!

The dough is thick, fluffy, and buttery.
I thought they used a perfect amount of sauce and the cheese was super gooey and greasy.
Made to perfection!!!
The pizza was so unbelievably good that there’s no question as to why the line is usually out the door around lunch time.
For this reason that’s why we beat the crowd and got there around 10am.
Another reason this place doesn’t fuck around is because once they run out of pizza dough for the day they just close up shop.
They are in THAT MUCH of a demand that they run out of stuff and can still afford to just close up for the day.

The prices are also very reasonable for such a great slice of pizza.
If you love unbelievably delicious, gooey, pizza for a good price make sure to get here early.
Pizza for breakfast has never been so good.

The finest gooey Boston pizza.
Look at all that gooey goodness from Galleria Umberto.

The rest of the day consisted of sightseeing and devouring pastries.
At night we had dinner in the North End(surprisingly NOT pizza) and checked out the bar scene.
Once we had our bellies full of alcohol it was time for some more pizza.


Our late night/early morning snack would be had at Little Steve’s Pizza(1114 Boylston St.).
It was probably the worst of all the pizza places we went to on this trip.
Not because it was bad but because the other places were absolutely exceptional.
Little Steve’s had a really great variety of different toppings.
The crust was all regular crust and the pizza itself was pretty decent.
Nothing to brag about, but it definitely cures your pizza cravings at 2am.

I’ve seen some horrible reviews about their customer service, but we didn’t experience any of it first hand.
If you’ve had a bad experience there you might feel better knowing that my friend pissed in their bathroom sink while I used their only toilet.
Sorry, but we both had to pee REALLY REALLY bad and I got to the toilet first.

That's a damn big slice from Little Steve's Pizza.
That’s a damn big slice from Little Steve’s Pizza.


That's what we call "a good fold".
That’s what we call “a good fold”.


A few days later we made it our plan to dedicate one whole morning to a little journey out to East Boston.
My friend said there’s nothing really worth seeing or doing out there except for visiting one of the greatest pizzerias in the whole United States.


Food & Wine Magazine listed Santarpio’s as one of the Best Pizza Places in the U.S.
Boston Magazine gave them “The Best Of Boston Award” 3 years in a row.
That is the type of recognition Santarpio’s has.(111 Chelsea St.)
We arrived at Santarpio’s about 30 minutes before they even opened and there were already 4 people waiting outside.

We didn’t make this 40 minute T ride to Eastie for just a slice or two either.
Nope, we were both getting large pizzas ourselves to devour in one sitting.
I ordered a Santarpio’s “Favorite Combination”, the Shrimp Scampi served White(no sauce).
My friend created his own; Sausage, Peppers, and Onions.
What an unbelievable choice he made.
When the Pizza’s came out we had to try a slice of each others masterpieces.
By all means his pizza undoubtedly blew mine away.
Aside from the crust it was the closest I’ve had to the pizza I ate in Venice, Italy.

On the contrary, mine was still very good.
My big mistake was probably getting a pizza with no sauce.
As a result I felt like I wanted to start fresh and get what he ordered.
The sauce was unbelievable and added a whole new element to his pizza.
At least now I know to get sauce the next time.

Shrimp Scampi from Santarpio's.
Shrimp Scampi from Santarpio’s.


Look at that gorgeous piece of work from Santarpio's.
Look at that gorgeous piece of work from Santarpio’s.


Afterwards my friend said that was the best Boston pizza he’s ever had.
Santarpio’s was indeed his favorite of the 4 places we visited.
I felt like my choice was a bit off at Santarpio’s, therefore Galleria Umberto was my favorite.
In conclusion I could see Santarpio’s winning if I had a different pizza and did a back to back contest between the 2 places.

There is without a doubt many other well known pizzerias in Boston that we unfortunately were not able to visit.
We had to make time for bakeries, seafood, and restaurants in Chinatown too, so that was the end of our pizza extravaganza.

Have you ever gorged yourself on Boston pizza?
What’s your favorite places?
Let me know in the comments.

Jeremiah Cooper

Jeremiah Cooper

Welcome to Live Life Extreme, a travel blog about thrill-seeking, adventurous travel through some of the largest cities to off the beaten path getaways.

My name is Jeremiah and I'm an Arizona desert rat in search of the next adrenaline pumping adventure.
Follow me as I show you What and What Not to do when visiting new places in search of Cheap Travel and Cheap Thrills.
Jeremiah Cooper

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