When I want go to Chianti I always stop in Vertine, a small castle near Gaiole in Chianti. It is surrounded by vineyards and olive groves and its really beautiful.
A bit of history
The first time the castle was included in a document was in 1013 and then again 1049 when it was attributed to Pietro di Pietro. Then in 1203 the castle became property of the famous Ricasoli family, that owned it since modern times.
During the 17th century the defensive walls were reinforced and restored and since then much has been changed. Vertine preserves its original medieval look enclosed in the massive walls.
What to see
What I like about Vertine is that is still alive and people live inside the castle. There are no shops or other tourist attractions expect one cafè serving also fresh cakes. I think this is its real beauty.
You can still see part of the walls, the keep arising next to the ancient gates to access the castle. Inside there is the Church of San Bartolomeo a Vertine, dating back to 11th century whose facade was rebuilt during 20th century in a Neo-Romanesque style. Inside you can admire part of renaissance frescoes by the Florentine school, while the beautiful Madonna dei Raccomandati by Simone Martini and the triptych by Neri di Bicci are now at the National Picture Gallery in Siena.
To reach Vertine you should drive to Gaiole in Chianti, by taking the state road Chiantigiana SS 408. When you are in Gaiole take the uphill street next to the church called Via Aldo Moro, and drive for about 3km.
The GPS coordinates are:
Latitude 43° 28′ 10,91″ N
Longitude 11° 25′ 03,23″ E