Well, I used the pineapple tart cutter I got in Singapore and they were tiny! Approx an inch across. Too much work!
I would use a 1.5 - 2 inch round cutter, but before you remove the cutter from the dough, use a round object (bottle, coffee tamper, to press a round indent into the dough. That way you get the little "bowl" to fill with jam.
BTW, I used canned pineapples, since fresh ones are a little finnicky this time of the year. I did not add sugar when I cooked it, since they were already sweet.
And the egg wash is essential when you are making the open faced ones... Otherwise the jam will get dried out.