Gaiole in Chianti
The city of Gaiole in Chianti is another important city within the Chianti Classico region, located along the river Massellone and on the road connecting Chianti to Valdarno. Thanks to this position, Gaiole has always played an important role as market center for the castles and towns nearby.
I have to say that the main attractions in Gaiole in Chianti are the wineries in its surroundings. Since it was a marketplace, it never had the need for defensive walls such as those in Radda in Chianti. In fact, its center was destroyed and rebuilt many times, and few buildings have been preserved from the past.
Despite this relative "newness", I still recommend a stop in Gaiole for a short walk before moving on to your next destination. In fact, the real attractions of Gaiole, beyond its Chianti Classico wine, are its surroundings which include beautiful castles and parish churches.
Among the most beautiful is the Parish Church of Spaltenna, displaying a valuable 15th century crucifix, the Castle of Vertine,a small medieval walled village, and the Abbey of Coltibuono, a former monastery now turned into a wine estate.
Another important castle in the area I highly recommend visiting is the Castello di Brolio. Founded by Longobards, it has been home to the noble Ricasoli family since the 12th century who has produced wine for centuries. Descendants of the family still live in the castle so while you can't visit the castle, I recommend you visit the gardens from where you can admire the breathtaking view of Chianti with the city of Siena at the horizon. Included in the entry ticket is a wine tasting at the estate's wine shop.