For those who stay on the Massetana, the valley road is easy and fun. Turn to the right and head through two medieval towns, Montieri and Gerfalco, both of which are worth exploring for their metal-rich hills. Then, farther on, the SP87 climbs towards Boccheggiano, and this is a great road with superb views. At the roundabout at Gabellino, a stop for a coffee at the bar will help you decide which route to take: betray the SP162 and hop over to Castiglione della Pescaia, or aim for Prata, to verify the famous quote, "You're as edgy as the roads in Prata."
Turn off to Prata and its historic fruit orchards, where they have local plants and rare trees on the verge of extinction. To visit it you have to skip the side road with the sea view and climb a little. Then, take the turn for Niccioleta, the mining town, which was the setting for a massacre by Fascist Nazis that took the lives of 83 miners, and the last chance to explore the area before heading back on the Massetana.