There’s a lot of hubbub over what is a “good pizza” or what makes a good pizza.  For me there are only a few places that make an outstanding pizza.  Before I describe one, I’ll tell you what I require in a solid pizza, as I’ve hinted at it before, but never actually defined my criteria for pizza quality.  They are:
1.) Good sauce - the sauce must be tart, slightly garlicky, but not too oily or overspiced.  For me, diced chunky tomatoes, garlic, salt and pepper is enough for a good sauce.
2.) Good dough - the dough must be flavorful and slightly buttery.
3.) Fresh toppings - This is rarely a problem, though I’ve seen some places use canned mushrooms and frozen spinach as toppings.
4.) Good oven - You can’t have good pizza that’s been run over a conveyor belt. Woodstone ovens make some of the best pizza that crispy on the outside (but not burnt) and still soft and a little chewy on the inside, and any pizza place that uses Woodstone automatically will be better than others.
5.) Balance - It’s important that there is a right balance of dough:sauce:toppings such that you can pick the pizza up by hand (for traditional slices).  If you’re eating Chicago deep dish, this need not apply.

That being said, probably my favorite pizza/calzone restaurant in Boston would have to be Picco in the South End.  While they do violate the “burnt” aspect for their dough, they hit all the marks for a good pizza.  But I think ultimately, a good slice of pizza is just a little burnt.  I decided to order the DIY calzone, which affords you three fillings for free, which for me was broccoli rabe, buffalo mozzarella, and mushrooms.  The sauce that came with the calzone was a simple garlic tomato sauce (check Item #1), though the fillings were fresh, it was an unfortunate combination of ingredients as the rabe was too bitter to be balanced by the sourness of the tomato sauce.  In hindsight I should have gotten something more tart like roasted red peppers instead of mushrooms.  But my biggest complaint is that cheese choice should not be an option as a filling!  You should be allowed three fillings and a choice of cheese for a calzone.  By shifting cheese into the filling selection field, you dramatically limit the variety of calzone that you can create yourself.  But you’re probably saying “Hey Cheese Sandwich Guy, why don’t you just shell out the extra $1.50 and add another topping?”  Because this is America my friends, and we shouldn’t have to!

While the calzone was pretty good (but limited in amazingness only by my unfortunate choice of ingredients), the ice cream at Picco is the star of the show.  Made fresh in-house, I don’t think there’s a better cup of ice cream in Boston (sorry fans of JP Licks or Toscanini’s).  There was a limited selection, as it is the dead of winter (you can get a much broader selection in the summer), but I ordered the coffee chip, which really melded the bold coffee flavor and the dark chocolate chips really nicely.  While I don’t often go to Picco, I do try to go just for the ice cream, which is great!

There is a limited menu selection for vegetarians, despite it being a pizza place where you can make your own pizzas/calzones.  So, you can definitely find something that you want at Picco, though it is common to fall into inappropriate flavor mixing traps such as the one I fell into.  But make sure you don’t leave before getting the ice cream, which is great.  For those reasons, I give Picco four cheese sandwiches.

Picco Restaurant
513 Tremont Street
Boston, MA 02116-6306 
(617) 927-0066