Your driver will pick you up directly at your ship in Livorno and after an hour and half driving through the Tuscan countryside you will reach San Gimignano. San Gimignano rises on a hill (334m high) dominating the Elsa Valley with its towers which date back to the 11 century.
The cultural and natural patrimonies have been recognized by UNESCO, but even more impressive is the medieval skyline made up of towers and the views from above and below them. The town increased in wealth and developed greatly during the middle Ages thanks to the "Via Francigena" the trading and pilgrim's route that crossed it. Such prosperity lead to the flourishing of works of art to adorn the churches and monasteries. On 8 May 1300 Dante Alighieri came to San Gimignano as the Ambassador of the Guelph League in Tuscany. In 1348 San Gimignano's population was drastically reduced by the Black Death Plague throwing the city into a serious crisis which eventually led to its submission to Florence in 1353. In the following centuries San Gimignano overcame its decline and isolation when it's beauty and cultural importance, together with its agricultural heritage, was rediscovered. Once in San Gimignano, other than admiring the famous towers, you can also see the "Duomo" or Collegiate Church, the "Palazzo del Popolo", the "Palazzo Nuovo del Podestà" (which is now the town hall), S. Agostino Church, the Museum of Holy Relics, and the infamous Museum of Torture, which displays early instruments of torture and reminds everyone that cruelty and violence existed even way back then.
On a lighter note, there are numerous shops which sell local products including the "Vernaccia" wine. During the transfer San Gimignano-Siena you will stop in Monteriggioni, without doubt one of the most classical and best known Italian walled town. The town was built by the Senesis in the years 1213-1219 on a hillock overlooking the Cassia Road. Its ideal position allowed controlling the Elsa and the Staggia Valleys in direction of Florence, the historic enemy of Siena. Here you'll have the chance to taste a true Tuscany meal in a typical trattoria. After lunch, we'll proceed to Siena, where you'll immediately notice an ancient and mysterious atmosphere floating through the little, narrow streets and squares. You'll feel as if you've stepped backwards in time.
Draped on its three hills, Siena is a very beautiful city to visit, a flamboyant medieval ensemble of places and towers cast in warm, brown, Siena-coloured bricks. It's soaring skyline is it's pride, dominated by the gothic cathedral (Duomo is one of the most spectacular in Italy and one of the few to have been built south of the Alps in full gothic style) and the taut needle of the Torre del Mangia and yet the shell shaped Piazza del Campo, probably captures the most attention and fame. It has been seen in films, photographs, and advertising campaigns. The bricks cover the sweetly sloping land underneath and are witness to many events in history, but the most intriguing is the "Palio" horserace, one of the most important things in the life of a Siena native. In the piazza on 2 July and 16 August there is a bareback horse race that was first recorded in 1283, but may have had its origins in Roman military training. On those days mayhem takes over this small town and non-natives can observe local patriotism at its best and worst. Any and everything will be done passionately to bring home the prize.
The prize is the "Palio", a banner to be shown off with pride for the whole neighbourhood it represents. At the end you will drive back to Livorno pier on perfect time to reboard your ship.
