Driving along the SP 408 road finding out the Chianti Castle Route, choosing one of its five itineraries, represents the best way to admire a surprising number of castles, villages, abbeys and ancient churches in the spectacular Chianti region.

- 1st Itinerary 

You get to Gaiole in Chianti where the Chianti Castles route begins. You turn right going up to Monti and San Marcellino villages and after that you get to Cacchiano. The Ricasoli family from Florence owned the Cacchiano castle since the XIIIth century but the stronghold was destroyed by the Republic of Siena twice, in 1478 and in 1530. If you go straight on again, you get to one of the most famous Castle of the Chianti, the Castle of Brolio (XIIIth century). It belonged to Florence since 1009 and then to the Ricasoli family. It was besieged by the Aragonesi in 1452, destroyed in 1478 and built again a few years later.

- 2nd itinerary 

You get to the castle of Monteluco, which was first recorded in 1176, just after some 7 kilometres past Gaiole in Chianti following the road signs to Lecchi. The Tower of Tornano is beyond the river and stands where Florence and Siena used to battle.

You can visit San Sano, on the left before getting to Lecchi. It's a village which dates back to the Middle Ages and has beautiful Romanesque buildings. Ama, Montebuoni, Casanova d'Ama and Poggio San Polo are after Lecchi. You can admire the wonderful Pieve (Parish church) of San Polo in Rosso (XIIth century, Poggio San Polo) which has been a fortess since 1300. It belonged to the Ricasoli family from Florence but it ws besieged by Siena in 1478. A few years later (1483) The Republic of Florence took control of it again.  

If you drive along the SP road, you turn left and get to to the villages of Adine, Galenda, San Giusto in Sacio and Le Selve, which is on top of a hill.

- 3rd itinerary 

The Castle of Meleto is on the right, 2 kilometres before Gaiole in Chianti. It was built at the end of the XIIth century. Siena took control of it in 1478 but it was besieged in 1529.

If you drive along the SP road to the Chianti hills, you can find the villages of Rietine, San Martino and Castagnoli. You drive past Monteluco, go back down to the Valdarno valley and you find some mountain villages, Nusenna, Starda, Fietri, Linari, San Vincenti. You can admire a wonderful Romanesque pieve, a parish church (700 A.D) in San Vincenti.

- 4th itinerary 

You get to the Pieve (parish church) of Spaltenna (XIthe century) if you drive along a road next to the church in Gaiole in Chianti. It's one of the most remarkable pieve of the region. Then, you get to the village of Vertine which date back to the XIst century and belonged to the Ricasoli family since the end of 1100.

The castle of San Donato in Perano was first recorded in 995. If you go along the road to Radda in Chianti, on the left you get to Vistarenni, a wonderful villa (XVIIth century) 

- 5th itinerary

At the Massellone on the southern end of Gaiole in Chianti, there is is a road on the left leading to Barbischio, a very charming villagage with some houses around an ancient tower. The castle of Barbischio (XIth century) is on the top of a hill.

After 5 kilometres, you get to a mountain pass in Coltibuono and you'll find the massive tower of Cancelli on the right side, an outpost of Montegrossi. The tower can be considered as a symbol of the ancient Chianti region and the Chianti League (Gaiole in Chianti, Radda in Chianti, Castellina in Chianti). Montegrossi is a village with a high tower nowadays.

After the pass, you turn left and get to The Abbazia (Abbey) of Coltibuono, an ancient church which dates back to the Xth century. It was restored and became an Abbey in 1037 with the Vallonbrosani friars. It got richer and richer but when Napoleon took control of it in 1810, the Abbey was auctioned. It is a flourishing farmhouse selling wine and olive oil nowadays. 

If you drive past three kilometres Badia Coltibuono to Radda in Chianti, you get to Cetamura del Chianti, an area of archaeological interest (ancient Greece, III century B.C)