San Gimignano to Etruscan Coast Vineyards: Private day trip

First mentioned in 1075, when its boundaries were being drawn, the town grew around the 11th century castle. Sitting on a hilltop, the brick bastion dominates the surrounding farmland, and it’s easy to see why it was attacked on several occasions, and has been owned by the Della Gherardesca family since the 13th century. Today, it’s still the first thing that emerges from the 5 kilometer long cypress boulevard made famous by Carducci’s “Davanti San Guido”. Nearby, the Church of Saints James and Christopher is the oldest building in the area and has maintained its medieval essence, even after its 1902 renovations. Of course, no visit to this charming village is complete without stopping to sample its world-famous wine, such as the Super Tuscan Sassicaia, which is considered one of the finest red wines in Italy.