Destinations Massachusetts North America


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.

This friend of mine is a total Foodie and 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.

He led me through the city on my own personal Boston Food Tour.
We had a lot of options to choose from.
But day one was strictly designated to Boston Pizza.

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 pizza that comes out of Boston.

We took a red-eye flight from Phoenix to Boston, and arrived right 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 a bit of variety as far as toppings go.
I had two different slices(Chicken and Cheese) and they were both as good as the other.

Boston 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).
And has over 80 restaurants throughout its cobblestone 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 good that there’s no question about why the line is out the door around lunch time.
For this is the reason we got there around 10 am.
Another thing about this place is 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 close up for the day.

The prices are also very reasonable.
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.

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 at Little Steve’s Pizza(1114 Boylston St.).
It was my least favorite 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 does have a great variety of toppings though.
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 2 am.

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 you might feel better knowing that my friend pissed in their bathroom sink.
Sorry, but we both had to pee REALLY REALLY bad and I got to the toilet first.
Boston Pizza
That’s a damn big slice from Little Steve’s Pizza.


Boston Pizza
That’s what we call “a good fold”.

A few days later we made a plan to dedicate one morning for a journey to East Boston.
The only thing worth doing there is visiting one of the greatest pizzerias in the 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 30 minutes before they 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 to 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 blew mine away.
Aside from the crust it was the closest I’ve had to the pizza I ate in Venice, Italy.

Mine was still very good.
But my mistake was 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 next time.

Boston Pizza
Shrimp Scampi from Santarpio’s.


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

And The Winner Is…

After Santarpio’s my friend said that was the best pizza he’s ever had. 
I felt like my choice was a bit off at Santarpio’s, therefore Galleria Umberto was my favorite.
If I chose a different pizza at Santarpio’s I could see it being my favorite pizzeria as well.

There are 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

By Jeremiah Cooper

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

My name is Jeremiah and I'm a photographer from Arizona.
I'm always in search of picturesque landscapes and 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.

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