David, sorry I assumed you would be driving down from Boston, but since you will be mostly on foot/cabbing it this is what I suggest for places that are all in or very close to the same general area (the village). Everything im listing is probably a $12 cab ride or less from each other, and much of this can be done on foot.
Motorino and Luzzos are right around the corner from each other. One trip and you can share a small pie at both places.
Keste and Johns, are right across the street from each other, another easy meal.
Grimaldes. This place is underrated now that there is so much other good NY pizza, but I feel like it really showcases the coal oven style nicely. Also, it is very close to all the other places I am recommending even though it is in brooklyn.
Lombardi's, combined with a walk down the little italy strip with the famous cheese/topping shops, Alleva, Dipaolos etc. (you should see this part of the city even if you dont try lombardis)
Finally, Isabellas Oven. This place rocks. It was introduced to me by Ed lavine and he actually told me that at that time (about two years ago) that it was one of his absolute favorite pizzerias in the city.
You could hit joes for a slice too since its really close to keste/johns. Honestly, I have had my best street slices at random spots while walking around the city. There are so many freakin pizzerias everywhere you look, and you can just use your eyes to clue you in on when you have a good one. The bar is so high compared to boston and you are bound to bump in to an amazing street slice just about anywhere.