Depart Florence in the morning with pickup from your centrally located hotel, and then settle in the comfort of your private vehicle during the drive to Tuscany.
On arrival in Siena, spend some free time wandering the city's historical center. See the Piazza del Campo and the Italian Gothic cathedral at the Palazzo Pubblico.
Leaving Siena behind for San Gimignano, you'll notice the pretty town's 13 towers from a distance. Relax as you amble past the weathered stone buildings and discover the town's hidden gems—it's an ideal place to purchase a meal accompanied by a glass of wine (own expense).
Then set off for Chianti for more free time. If you choose, you can your a local winery and get a sense of traditional Tuscan life (own expense), and learn how wine is processed and produced.
Afterward, you're dropped off at your hotel in Florence.