There are two kosher restaurants in Florence. One is around the corner from the synagogue and is called Ruth's. It is fish/dairy. There is also a kosher mini-market nearby that sells sandwiches and some prepared and eat-in food. The family that runs it is very nice and does private event catering. There are also a couple of kosher butchers.Stitchy could survive Pitti. It would be legendary.
I don't mean to disappoint you, but beware. I wore a new NSM suit yesterday and the worktag in the trousers specifically said "pants" not "pents". It felt like I has ordered in a Chinese restaurant off the English menu.
I can't say whether it is enough, but reports from the training academies and apprentice programs on Savile Row and in Italy is that young people ARE entering the trade. And it should not be surprising. Those are good jobs in places where jobs are scarce.