First slide

Tuscany Tour in Siena and San Gimignano

Day tour in Tuscany visiting Siena and San Gimignano with private limousine service and English speaking driver.


Sightseeing tour to Siena and San Gimignano with transportation with private driver from Florence, Cortona, Montepulciano, Montalcino, Pienza, Siena area, San Gimignano area, Chianti (Radda, Gaiole, Greve, Castellina), Arezzo, Perugia, Assisi and from all Tuscany, Umbria and Italy.




  • Private daytrip in Siena and San Gimignano from Tuscany with private English speaking driver and transportation
  • Scenic itinerary through the beautiful landscapes of Tuscany
  • Learn all about the history of Siena and San Gimignano and view the beautiful art and architecture
  • The best of Siena strolling the city center through Piazza del Campo and the Cathedral
  • View the charming streets and squares of San Gimignano and enjoying amazing views of Tuscany from its towers





Discover Siena and San Gimignano and the charming Tuscan countryside with a one day tour from all Tuscany with a private car service and English speaking driver.


Your Tuscany day tour will start in Siena with the suggestive Piazza del Campo, the heart and main square of the city with the Town Hall, and with the Torre del Mangia, more then 300 feet high, from where you can enjoy a beautiful view of the city and the Tuscan 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 the excursion in Siena walking and enjoying the scenery of its typical city streets and charming squares.


Leaving Siena, your tour in Tuscany can include a stop at Monteriggioni, a medieval castle which encloses a charming village.

This area in the heart of Tuscany is also very well known for the production of excellent extra vergin olive oil and for some of the finest Tuscan wines. The stop for lunch can be organized in a local family-run winery, having lunch on a terrace with a beautiful view of the Tuscan landscape with a traditional Tuscan tasting menu paired with the excellent Tuscan wines.


Last stop of your Tuscany tour will be San Gimignano, where you will have the chance to visit the extraordinary and original medieval town center with the high Medieval city walls, the Town Hall, and the tall stately towers, from which the name of Medieval Manhattan. It will seem as if you are truly reliving that unique atmosphere of the Middle Ages. The Tour in Tuscany ends strolling and exploring the San Gimignano town center, with the typical craft shops and Italian Gelaterie, sitting outdoors, you can enjoy the excellent Italian gelato and the Tuscan atmosphere of this gorgeous Tuscan hill town.

Departure available from:

  • The day trip in Tuscany visiting Siena and San Gimignano is a private tour available from all Tuscany, Florence, Cortona, Montepulciano, Montalcino, Pienza, Siena, San Gimignano, Chianti (Radda, Gaiole, Greve, Castellina), Arezzo, Perugia, Assisi, Orvieto, Todi, Spoleto, Spello, Gubbio and from all Umbria and Italy.



  • approximately 8 hours



  • Qualified and professional English speaking driver
  • Luxury vehicle (Mercedes-Benz or equivalent)
  • Head office assistance and insurance coverage
  • Complimentary water
  • Wi-Fi on board
  • Local tour guide for walking tours (on request)
  • Traditional Tuscan lunch in a winery with wine tasting (on request)

Siena: 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.

Do not miss! Piazza del Campo, Palazzo Pubblico, Fonte Gaia, Torre del Mangia, Cathedral, San Domenico Church


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.

Do not miss! Piazza della Cisterna, Medieval Walls, Torre Grossa, Torre Rognosa, Palazzo del Municipio

Get Tours recommends

Guided day tour in Tuscany with private car service and driver for visiting Montepulciano, Pienza, Montalcino and Val d’Orcia.
Tuscany day tour visiting Siena and San Gimignano with private limousine service and English speaking driver from all Tuscany.
Sightseeing day tour of Florence with private limousine service and English speaking driver available from all Tuscany, Umbria and Italy.
Wine tour in Montepulciano and Montalcino wine countries; guided wine tasting experience in Tuscany with private driver and wine expert.
Guided food & wine tour in Chianti, the heart of Tuscany, with private driver. Scenic itinerary through the Chianti wine region with wineries visits and wine, cheese and olive oil tastings.