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Siena and San Gimignano Tour

Private Driver Service with luxury sedans, minivans, minibuses in Tuscany for a Siena and San Gimignano Tour

Along a scenic road through the hills of Tuscany, you will arrive at San Gimignano, where you will have the chance to visit the extraordinary medieval centre which still preserves the original structure of that time. The high Medieval walls, the Town Hall, the tall stately towers, from which derives the name of Medieval Manhattan: this is the extraordinary scene ahead of you as you walk through the streets of the town. It will seem as if you are truly reliving that unique atmosphere of the Middle Ages. Leaving San Gimignano, tour includes a stop at Monteriggioni: it is a medieval castle which encloses a charming village. Arriving in Siena you will visit Piazza del Campo, the heart of the city with the public building, and with the Torre del Mangia, more then 300 feet high, from where you can enjoy a beautiful view of the city and the Siena countryside. Piazza del Campo is also the location where, every 2nd July and 16th August, the famous Palio di Siena is raced (horse race of Medieval origins). You will inevitably visit the Cathedral: one of the most famous examples of Romanesque-Gothic style, ending in the city streets, with the typical craft shops and Italian bars where, sitting outdoors, you can enjoy the atmosphere of this fantastic city.


Duration: approximately 8/9 hours

Included: comfortable air conditioned vehicle, private driver (English speaking) at your disposal for duration of tour, taxes, fuel, parking, motorway tolls, meal of the driver, and of “our best”!

Not included: lunch, entrance fees to monuments or museums, wine tasting, and anything not specified as “Included”.

It is possible for the tour to leave from locations in Tuscany and Umbria, within the areas in which we operate (click here to view map) and, based on logistics, the specific programme can be modified.


San Gimignano: Probably of Etruscan origin, the town was able to emerge and assert itself during the Medieval period. In 1199 it became a free municipality, and in the following century consolidated its strength and independence to balance on a flourishing trade of agricultural commodities, such as saffron, and a strong financial economy. This allowed it to develop a rich and powerful aristocracy that enriched the city itself of public works (residential towers). For its geographical position, it passed many times between the hands of the Guelfs and Ghibellines, and between Florence and Siena, then, exhausted and hit hard by the Black Death of 1348, it surrendered voluntarily and permanently to the republic of Florence.

Piazza della Cisterna, Medieval Walls, Torre Grossa, Torre Rognosa, Palazzo del Municipio

The city has Roman origins and was founded during the reign of Augustus. In Medieval Times it was an obligatory stop along the Via Francigena (important road linking Canterbury, France, Rome and Jerusalem) and thanks to this, it was able to increase trade and economy, becoming one of the richest cities of the Middle Ages. It became a free municipality, guided  by a Ghibelline administration, and soon found itself colliding with other neighbouring cities. Very famous is the battle of Montaperti in 1260, where the Ghibelline army of the cities of Pisa, Arezzo, Cortona and above all, Siena, supported by the Emperor, had the best counter to the Guelf army, supported by the Pope, the city of Bologna, San Gimignano, Perugia, Orvieto and above all Florence. It was an epic battle, which marked the supremacy of the republic of Siena on the national and international scene. In what followed, however, the terrible defeat at the battle of Colle Val D’Elsa, and above all the black plague of 1348 which determined a strong crisis and a gradual downsizing of the city for Florence, in which the Senese republic had finally succumbed in the XVI Century. Worthy of mention is the foundation of the Monte dei Paschi di Siena Bank in 1472, which the Vatican used to address, and which today represents the oldest bank in activity in the world.

Piazza del Campo, Palazzo Pubblico, Fonte Gaia, Torre del Mangia, Cathedral, San Domenico Church