Travel north into the first Chianti hills and take a walk around Monteriggioni, a medieval and perfectly preserved fortress with a complete ring of city walls and turrets built in the 13th century and mentioned by Dante in his Divine Comedy: this was once Siena’s main bastion of defense against the armies of Florence. Enjoy its quiet and charming atmosphere browsing the alleys and shops of local crafts and products, or lighting a candle in the local church as the pilgrim's once did.

Continue to the fascinating town of San Gimignano, one of the most characteristic hilltop towns of Tuscany, with its many austere medieval towers that defiantly survived the centuries and are still proudly standing today. Recognized as a UNESCO site of world heritage, this city is a great testimony of medieval architecture. Walk along the ancient route of the Via Francigena, the main route that took all travelers and pilgrims of Europe to Rome and the Holy See. The bustling San Gimignano flourishes with artisanal boutiques of the local trades and stores, selling the towns famous ‘red gold’ or saffron spice as well as the Vernaccia white wine, so traditional and old that Dante mentions it in the 13th century.

Brief visit to the minature museum and marvel at what San Gimignano looked like during the Middle Ages

After working up an appetite browsing squares, streets, churches and stores of San Gimignano, visit a small family-run farm and enjoy a traditional Tuscan lunch prepared using the farm's own seasonal products. During lunch you will taste dishes prepared with saffron accompanied by the refreshing Vernaccia white wine. After lunch, continue on the panoramic roads towards Volterra, the ancient Velathri, a city that harmoniously combines Etruscan and Roman ruins with medieval and Renaissance architecture, with the unavoidable modern buildings and furnishings. Visit a small, artisanal workshop and meet the craftsmen that have been working the local alabaster for decades. Witness this ancient art of sculpting this stone into precious masterpieces.

Enjoy leisure time walking along the streets of the historical centre of Volterra, visiting the town’s famous Etruscan museum or simply marveling at the millennia old Etruscan arch, the Roman theatre or the more modern monuments and shops in town. On some occasions the itinerary might vary a little. In this case, the tour could be slightly modified but will maintain a similar general imprint, of the same duration and with all the same inclusions.