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Tuscany Tour in Cortona and Montepulciano

Private guided tour in Tuscany with English speaking driver visiting Cortona and Montepulciano.


Sightseeing day trip to Montepulciano and Cortona with transportation with chauffeured sedan and minivan from Siena, Florence, Cortona and Montepulciano area, Montalcino, Pienza, San Gimignano, Chianti, Arezzo, Perugia, Assisi, Orvieto, Todi, Spoleto, Spello and from all Tuscany, Umbria and Italy.




  • Private daytrip in Cortona and Montepulciano from Tuscany with private English speaking driver and transportation
  • Scenic itinerary through the iconic Tuscan landscapes of the Valdichiana
  • Learn all about the ancient history of Cortona and Montepulciano and view the beautiful art and architecture
  • Cortona and Montepulciano: towns Under the Tuscan Sun. View their charming streets and squares and enjoying amazing views of Tuscany
  • Behind the scene: Vino Nobile di Montepulciano, one of the best Tuscan wines





Tuscany guided day tour with private car service and English speaking driver visiting Cortona and Montepulciano, two of the most beautiful Tuscan hill towns, immersed in fields of sunflowers and vineyards in the gorgeous Tuscan rolling hills of the Valdichiana valley


Tour in Tuscany starts in Cortona, with the impressive Etruscan town walls, its characteristic medieval streets and squares, and the breathtaking panoramic views over the beautiful surrounding Tuscan countryside. Cortona is also recently made famous by Frances Mayes with her book and film “Under The Tuscan Sun” and the her villa Bramasole; this is your chance to play the part and feel like you’re in a real film-set! It is definitely one of the best places where art, history, environment and tradition blend perfectly, where you can taste traditional Tuscan cooking and where you can still find an authentic Tuscan lifestyle.


The gorgeous Tuscan countryside in between Cortona and Montepulciano with fields of sunflowers, vineyards, olive groves and the gentle rolling hills of the Valdichiana is also famous for the excellent wine and extra virgin olive oil production, so lunch stop con be arranged in a local farm and winery immersed in the Tuscan rolling hills and it can include a wine & EVO oil tasting as well as a typical Tuscan menu, giving you a special insider view of the local products and cuisine.


Driving on scenic roads, the tour in Tuscany moves to the beautiful Tuscan hill town of Montepulciano. Rich of monuments of the Middle Ages and the Renaissance, Montepulciano is a delightful town, full of charm, where also one of the best Tuscan wines is produced: the Montepulciano Nobile DOCG wine and you should definitely not miss the chance to visit one of the many historical wineries in the Montepulciano underground with their ancient atmosphere and wine tradition.

Departure available from:

  • The day trip in Tuscany visiting Cortona and Montepulciano is a private tour available from all Tuscany, Siena, Florence, Cortona, Montepulciano, Montalcino, Pienza, 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)
  • Winery visit and traditional Tuscan lunch with wine and extra virgin olive oil tasting (on request)

Cortona: The foundation of the city is characterized by many legends and is lost in the mists of time, but it is agreed that it was founded by the Umbrians, and then conquered by the Etruscans. During Etruscan times (IX-IVth Centuries BC) the city was one of the 12 lucumonies (city states) belonging to the league and then passed under the domain of Rome in 310 BC. During the Roman period the city went through a thriving and prosperous phase, even if it had to powerlessly assist in the massacre which occurred during the Battle of Lake Trasimeno, between the Carthaginian Hannibal and the Roman army. After a period of decline in the high middle age, the city reflourished during the municipal and renaissance period (XII-XVI Century). It was exactly during this time that Cortona was a free municipality with its own currency, and then became a “signoria” ruled by the Casali family, often found either fighting or allied with many of the nearby cities, such as Siena, Arezzo, Perugia and Florence. It is exactly in 1411 that Cortona came under the control of Florence, following its fate until 1861, the year in which it became part of the unification of Italy.

Do not miss! Etruscan Walls, MAEC (Museo dell’Accademia Etrusca – Etruscan Museum), palazzo del Municipio (Town Hall), Via Nazionale (Main Street).

Of Etruscan origin (IV-III BC), the city knows the real phase of splendor during the medieval and renaissance period, marked by political prestige, flourishing economy and cultural value. Coveted by Florence and Siena, it grows and develops in the municipal period, until 1390, the year in which it passed under the control of Florence, where Montepulciano represented a territorial outpost in the area of Siena. The growth continues in the Renaissance, giving illustrious names to the church, the arts, letters and to politics of that period.

The city is also famous for the richness and excellence of its vineyards, from which is produced the Nobile of Montepulciano DOCG wine. It is one of the oldest Italian wines (testimonies from 783) and is characterized by Sangiovese and Canaiolo grapes, with a minimum aging process of 2-3 years.

Do not miss! Piazza Grande (Main Square), Cathedral, Palazzo del Municipio (Town Hall), Gattavecchi Winery, Redi Winery

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