Florence, Chianti and Siena in 3 days
Ciao Annette,
Have you been to Florence or Tuscany before? If this is your first time, I heartily recommend you spend at least a full day in
Florence. You can drive into Florence but park in the various car parks along the "viali circonvalazione" such as the two in the Piazza Beccaria area (one is Beccaria, the other is San Ambrogio). You can then walk into the historical center in less than 15 minutes without worrying about getting fines for having driven into the ZTL (limited traffic area that requires special permits).
Then spend another day driving around
Chianti, to the various villages - such as Greve, Radda, Castellina, Gaiole.... you don't need to visit them all, but driving through gives you a sense of what Chianti is, with its vineyards, hills, olive groves. If you have time, head out towards
San Gimignano, on the western edge of Chianti.
Spend your third day in
Siena - great rival of Florence for centuries, it went into decline while Florence flourished under the Renaissance. This means it stayed largely medieval in aspect, so it is a great way to see how different these two cities are, since they are Tuscany's top destinations.