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Cortona and Montepulciano Tour

Private Tour of Cortona and Montepulciano with luxury chauffeured sedans, minivans, minibuses for hire

Cortona is a marvellous town, and a real gem of Tuscany. With a long history behind it, evidence to which are the impressive Etruscan walls, which enclose its characteristic medieval quarters, it is perched on a hill which dominates the Valdichiana, where you can enjoy breathtaking panoramic views over the beautiful surrounding Tuscan countryside and Lake Trasimeno. Recently made even more famous by Frances Mayes with her book and film “Under The Tuscan Sun” , Cortona is definitely one of the best places where art, history, the environment and tradition blend perfectly, where you can taste traditional and authentic Tuscan cooking, and where you can still find tranquillity and a good lifestyle. The other stop on the tour is Montepulciano which is reached by scenic roads through fields of sunflowers, vineyards and sweet hills. With a historical centre which shows indelible signs of the Middle Ages and the Renaissance, Montepulciano is a delightful town, full of charm, where one of the best wines of Tuscany and Italy is produced: Montepulciano Nobile DOCG wine, which you should definitely not miss the chance to taste in one of the many wine shops in the town.


Duration: approximately 7 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.


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.    

Etruscan Walls, MAEC (Museo dell’Accademia Etrusca), palazzo del Municipio, Via Nazionale (Corso).

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 Vino Nobile of Montepulciano DOCG. 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.

Piazza Grande, Cathedral, Palazzo del Municipio, Gattavecchi Winery, Redi Winery