July and August are hot and busy, particularly in Florence; winter is quiet and atmospheric, ideal for city sightseeing and food, if cooler for the countryside.
Three ways we’d do it
Road trip · 7–12 days
Tuscan Food & Wine
Florence to the vineyards of Chianti and the Val d’Orcia.
Florence → Tuscany
Rail journey · 7–10 days
Tuscany Without a Car
Florence, Lucca, Pisa and Siena, all reachable by train and bus.
Florence → Tuscany