Bus tours and other specialty tours of the Chianti
With an organized tour (widely available from Florence and Siena), you can sit back and let others do the work and the driving, and not worry about getting lost (or overindulging at the wine tastings). Keep in mind that many of these tours only go to the places that can accommodate hordes of visitors, have their own fixed schedules, and eliminate some of the adventure that makes travel fun. Smaller tours and private guides are available as well.
Keep in mind that wine-tasting tours aren’t the only option; you can combine them with cooking classes, biking or hiking trips, and shopping.