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Tuscany Tour in Siena and Chianti Wine Country

Guided day trip in Tuscany with private English speaking driver and limousine service for visiting Siena and the Tuscan wine region in Chianti.


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




  • Private daytrip in Siena and Chianti from Tuscany with private English speaking driver and transportation
  • Scenic itinerary through the iconic landscapes of the Chianti wine region
  • Learn all about the history of Siena and view the beautiful art and architecture visiting Piazza del Campo and the Cathedral
  • The picturesque Chianti villages strolling their charming streets and squares and enjoying amazing views of Tuscany
  • Behind the scene: Chianti, one of the most famous Tuscan wine regions





A guided one day tour in Tuscany for visiting the beautiful and charming city of Siena, and in the gorgeous sceneries and landscapes of the Chianti wine region with private English speaking driver and car service.


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 in the charming city streets, with the typical craft shops.


The tour in Tuscany continues visiting the Chianti wine country with beautiful sceneries and landscapes, of vineyards, medieval castles and small hill towns. Chianti region is very well known for one of the best Tuscan wines produced in this area: the Chianti Classico wine Docg and for wine lover we can set lunch in one of the best Chianti winery, with a private tasting session of the top Tuscan and Chianti wines and with a typical Tuscan menu lunch.


Last part of your Tuscany tour will be dedicated to visit the lovely villages of Radda in Chianti and Castellina in Chianti, exploring their charming town centers with their picturesque views, living an authentic and intimate experience of the Tuscan lifestyle.

Departure available from:

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



  • approximately 7/8 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)
  • Winery visit and wine tasting (on request)
  • Traditional Tuscan lunch 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.

Don’t miss! Piazza del Campo, Palazzo Pubblico, Fonte Gaia, Torre del Mangia, Cathedral, San Domenico Church


Chianti: the area of the hills of Chianti does not have such well defined borders, but Castellina, Radda and Gaiole, are commonly considered to be part of this area. Over the centuries the area has spread to the area of Panzano and Greve, which in 1972 added to its name, the suffix “in Chianti”. Historically, it is an area lived in since Etruscan times, but is definitely an optimum example of a feudal society of high middle age. There are numerous testimonies of scattered castles in the area, built between the IX and XIII Centuries, to protect the small hamlets and residential areas, on which the surrounding county depended. From municipal times to the renaissance, because of its geographical location, which marked the border between the territories of Siena and Florence, very often the area represented a field of battle and conquest on behalf of both republics, which alternated the control of the region. The area is very famous for the production of the Chianti Classico DOCG, a red wine produced with sangiovese (80 – 100%). This wine has an intense ruby colour and dry taste, is full bodied and velvety, and lends itself very well to further aging.

Don’t miss! Castellina in Chianti, Radda in Chianti

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