What are the best itineraries for a road trip in Tuscany?

For a first road trip, I would choose Florence–Chianti–Siena–Val d’Orcia on 4 à 5 jours : you combine cities, small roads and landscapes, without spending your whole stay behind the wheel. From Florence, follow the SR 222 towards Greve and Castellina in Chianti, then head to Siena; allow about 70 km between Florence and Siena via the Chianti, but rather 18. 2 to 3 hours with the bends and the stops. Continue towards Pienza, San Quirico d'Orcia and Montalcino : plan at least two nights in the area so you don't rush from one stage to the next.

If you prefer the coast and the south, start from Grosseto to Castiglione della Pescaia, the Maremma park, then Pitigliano and the springs of Saturnia. It's a loop to spread over 3 à 4 jours ; the journeys look short on the map, but the secondary roads lengthen the times. For a one-week stay, you can link the two itineraries by passing through Siena, but avoid changing accommodation every evening. Spring and September-October are often more pleasant for driving than in the height of summer, when heat and traffic complicate sightseeing.

In historic centers, park on the outskirts: the ZTL are limited traffic zones, and a rental car is not automatically allowed to enter. Also check whether your accommodation can register your license plate before you enter. For Florence or Siena, the car is mainly useful for the rural stages, not for visiting the center.