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Tuscany Tour in Cortona and Arezzo

Tour “Under the Tuscan Sun” visiting Cortona and Arezzo with private car service and English speaking driver.


Daytrip in Tuscany to Cortona and Arezzo with private transportation from Siena, Florence, Cortona and Arezzo area, Montepulciano, Montalcino, Pienza, San Gimignano, Chianti, Perugia, Assisi, Orvieto, Todi, Spoleto, Spello and from all Tuscany and Umbria.




  • Private daytrip in Cortona and Arezzo from Tuscany and Umbria with private English speaking driver and transportation
  • Scenic itinerary through the beautiful landscapes of Tuscany
  • Learn all about the ancient Etruscan history of Arezzo and Cortona, and view their medieval architecture
  • The best of Arezzo strolling Piazza Grande and admiring the Piero della Francesca’s masterpieces
  • Cortona: the town Under the Tuscan Sun. View its charming streets and squares and enjoying amazing views of Tuscany





Tuscany day tour with private limousine service and English speaking driver visiting Cortona, one of the most beautiful Tuscan hill town, and Arezzo, a gorgeous and authentic Tuscan medieval city, through the charming 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!


Cortona area is also famous for the excellent wine and extra virgin olive oil production, so lunch stop con be arranged in a Tuscan farm immersed in the Tuscan rolling hills and it can include a wine & olive oil tasting as well as a typical Tuscan menu, giving you a special insider view of the local products and cuisine.


Tour under the Tuscan sun continues in Arezzo, an elegant Tuscan city with a characteristic medieval historical center where you can visit the Saint Francis Basilica, with frescoes by the 15th Century painter Piero Della Francesca, San Domenico Church with the amazing Cimabue wooden crucifix, and the impressive Gothic Cathedral. The center of the city is full also full artisans, antique shops and Goldsmiths, activity for which Arezzo has always been considered a capital of the finest Italian jewelry. As for films, Arezzo is no exception: it will be also fun to walk the streets where the masterpiece and winner of three Oscars was filmed: Life is Beautiful.

Departure available from:

  • The day trip in Tuscany visiting Cortona and Arezzo is a private tour available from all Tuscany, Siena, Florence, Cortona and Arezzo area, Montepulciano, Montalcino, Pienza, San Gimignano, Chianti (Radda, Gaiole, Greve, Castellina), 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 local farm with wine and 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).

From archaeological findings it seems that the first settlements date back to the Palaeolithic period, but the first real townhouses came with the Etruscans in the IXth Century BC. It prospered and thrived during this period, and was one of the twelve cities of the state of the league, soon having to deal with the emerging power of Rome, to which it succumbed in the 3rd Century BC. After a dark period in the high middle age, it was after the year one thousand that, becoming a free municipality, it developed and became one of the most hostile cities of Florence and Siena. Famous is the battle of Campaldino in 1289, in which the poet Dante Alghieri participated, and saw the victory of the allied army of Florence and Siena. It was exactly under the dominion of Florence, that at the end of the XIVth Century, the city ends, and the story follows until the annexation of Italy in 1861. The city today is one of the most important places in the world for the working of gold, and is well known also for its antiques fair, which takes place on the first Sunday of each month.

Do not miss! Piazza Grande (main square), Cathedral, Frescos of Piero della Francesca, Saint Francis Basilica, San Domenico church.

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