Without knowing your sister, it's a difficult question. Unfortunately there is no restaurant in the Villages that is above mediocre. For food Cane Garden is currently above the average. For setting maybe one of the town squares where you can eat outside and listen to music. (nothing like a town square in Naples) SS Demshaws, LSL Red Sauce or City Fire, BW World of Beer or Riccardi's.
Go in a golf cart where ever you go as that is also unique to the Villages. Maybe go someplace off campus for dinner then come back and go to a square for drinks and dancing.
I think it is so sad that when someone wants to go someplace nice for dinner, anything in the Villages doesn't cut it. And I know many will say lots are OK and yes, they are just OK, but I can go almost anywhere, any city or town and find a place better then anything here.
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Life is to short to drink cheap wine.
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