where can I find a quaint village to settle down?

Europe won't be as warm in winter as Florida, but you could start by exploring the Mediterranean coastline.

Your profile doesn't say where you live, but if you're a US citizen, you face all sorts of hurdles moving to Italy. More info here:
Italy Expats

As for warm weather year round, you might consider Sicily, although it depends on what you consider warm. Italy is not in the Tropics.

Last year on a Regionale train I met a young soldier, husband and father of two young children, who told me that he had been all over Italy and wanted to move his family to Lecce, the best place to live in Italy, he said.

It's in the bottom of the heel.

Check out boards like Expats in Italy. Rick's board is for travelers.

If you are looking for warmth, the only place I could suggest would be Sicily. Just don't go to a place like Enna or anywhere with a higher elevation as you will be very cold. The further south you can get in Europe, the better.

Are you moving to Italy permanently or just settling down for a couple of months? Unless you are a EU citizen, moving to Italy for over three months requires an immigration visa, which is given only in certain circumstances and after lengthy bureaucratic procedures. Contact the closest Italian consulate to you for details.

Little towns are everywhere. There are 8057 municipalities in Italy and on average each municipality, seated in the main town, includes 7 or 8 smaller towns or villages (called "frazioni" or fractions). So there are about 60,000 to choose from and many are quaint and full of charm.

In terms of good weather year around, it depends on what your tolerance for cold is. If you live in the upper Mid West, any place in Italy will be much warmer in winter. Temperatures in Northern Italy are in the same range you will find in Oregon, with variations due to altitude and between the coast and the interior. central and southern Italy have a Mediterranean climate similar to Central and Northern California. Like in California, coastal areas have milder climates than the interior, and temperatures drop as you go up in altitude (lots of mountains in Italy). Also temperatures are higher in the south, all other things being equal. One thing to consider is that the Adriatic coast is generally colder in winter than the Tyrrhenian coast. That's because of winter winds coming down from Eastern Europe and the Balkans (the Eastern Alps are also lower and don't protect as much from those winds).