Like so many towns that spurted up along the Florence border, it was considered a strategic military outpost, protecting the medieval city of Florence from invasion. But San Casciano didn’t start life that way; it was a classic market town set low in the valley and thus it grew-up with hardly any defenses making it an easy target for hostile takeovers.
It was until the 1400’s when Florence finally decided that San Casciano needed to be more well endowed, making it an integral part of their defences, did the impressive city walls appear. These are the very same that you see now as you walk around the city. Like many towns, once peace was achieved between Florence and Siena, the powerful military stance was no longer required thus there was no need to maintain the city. The loss of economic trade which once supplied the military contingency and the activity that surrounded it, slowly ate away at their eco-social prowess until San Casciano became just another little town in Chianti.
Unfortunately, most of the town was destroyed by the retreating Germans and the advancing allies. However, the town quickly overcame this and rebuilt the many churches, homes and streets leaving a small but active community which organizes many events and reinforce many local traditions throughout the year.

The Antique Walls of San Casciano
San Casciano has dedicated time and resources to create real sidewalks throughout the little town, making it truly a pleasure to walk around and explore. The city walls are parallel with a wide sidewalk where with a leisurely stroll around, you can soak up some of that great Chianti weather and admire the massive city walls. The walls built in mid 1300’s measured 7 meters tall and over 1200 meters in length with two principal gates in the direction of Florence and Siena and two minor gates in the direction of Empoli and a "prato" (a large grassy field). Throughout the city and its streets, parks and cafes you will notice that the architects have managed to mix modern art accents almost seamlessly with the antique structures. A prime example is the statue of a stag (by artist Mario Merz) walking along the top of the antique city walls.

Florence offers so many unique experiences and events that it will create memories which will live with you long after your holidays in Tuscany are over. All roads, inevitably lead to Florence, so examine our maps and find where you can revel in the awe of a historic skyline, and admire the architectural lines that inspired designers worldwide. The churches Santa Croce, San Miniato, Santa Maria Novella and San Lorenzo house some of the more important tombs, mosaics and frescoes while the museums will delight you with artwork, bronzes and marble statues and many treasures.

The Campo is dominated by the red Palazzo Pubblico and its tower, Torre del Mangia. Along with the Duomo of Siena, the Palazzo Pubblico was also built during the same period of rule by the Council of Nine. The civic palace, built between 1297 and 1310, still houses the city's municipal offices much like Palazzo Vecchio in Florence. Its internal courtyard has entrances to the Torre del Mangia and to the Civic Museum. If you feel energetic, a climb up the over 500 steps will reward you with a wonderful view of Siena and its surroundings.
The Museum, on the other hand, offers some of the greatest of Sienese paintings. The Sala del Concistoro houses one of Domenico Beccafumi's best works, ceiling frescoes of allegories on the virtues of Siena's medieval government. But it is the Sala del Mappamondo and the Sale della Pace that hold the palaces's highlights: Simone Martini's huge Maestà and Equestrian Portrait of Guidoriccio da Fogliano and Ambrogio Lorenzetti's Allegories of Good and Bad Government, once considered the most important cycle of secular paintings of the Middle Ages.