The short trip from the medieval, walled town of Radda-in-Chianti to Florence is only 32 miles (50 km). It is accessible with a car, whether you choose to self-drive or hire a private transfer, and is about 50 minutes in total. Though parking and driving in Florence can be tricky, having a rental car is handy in Tuscany—there are many worthwhile short trips you can take within the region, including Siena, Lucca, and Pisa.
Visit Radda-in-Chianti in this 6-day itinerary, which includes a wine tour, exploring villages of the Italian countryside, and even a few days in Rome. For something more active, try this 5-day cycling tour from Florence to Siena via Radda-in-Chianti.
By Rental Car or Private Transfer
Duration: 50 minutes (longer with stops and traffic)
On this short journey, you'll take the Raccordo Autostradale Firenze (a major superhighway) for the majority of the drive. This route does have tolls, so plan accordingly.
The historical center of Florence is a Limited Traffic Zone (ZTL) and only vehicles with special permits are allowed to enter this area. If you do, there are high fines associated with it so try to avoid it! However, there are a number of car parks around the center and paid parking lots and garages. If you are able to find paid street parking be prepared for a longer walk. It may be the least expensive option with your car, but you may find yourself parking in less centrally located areas.
You can easily find parking around Lungarno della Zecca Vecchia as well as Piazza Beccaria and Lungarno della Zecca Vecchia are great options if you're able to get there and get you close to all of Florence's main attractions.
Hiring a driver is another great option, especially as part of a broader Tuscany itinerary. Florence itself is extremely walkable, and you can forego the hassle of parking or navigating the ZTLs (a legitimate point of stress in Florence).