Wow i'm surprised no one has mentioned Garvino's Cigar and Wine bar here in The Villages.
Paul Price plays guitar favorites (Jazz) on Thursday nights starting at 7:00.
Garvino's has quite possibly the nicest bunch of people working there that I have ever met. They really do treat you like family. No I do not work for them. ;D
Garvino's website -
http://garvinos.homestead.com/index.html