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Two Tuscan hill towns made famous by 'Under the Tuscan Sun'.
A private, chauffeured day trip through the Tuscan countryside to the hill towns of Cortona and Montepulciano, with a light lunch along the way.
Enjoy the luxury of a private, chauffeured drive through the Tuscan countryside, exploring the impressive sights and historic attractions of Cortona, then eating a light lunch before strolling through the charming streets of Montepulciano.
A popular starting point — every Voyzo itinerary is fully customizable, so we'll shape the order and stops around your group.
Hotel pickup included in Florence.
Explore the historic town made famous by 'Under the Tuscan Sun'.
Stroll the medieval streets of this Vino Nobile wine town.
Back to your hotel, home, or the airport — whenever your day wraps up.
A private, chauffeured day trip through the Tuscan countryside to the hill towns of Cortona and Montepulciano, with a light lunch along the way. Enjoy the luxury of a private, chauffeured drive through the Tuscan countryside, exploring the impressive sights and historic attractions of Cortona, then eating a light lunch before strolling through the charming streets of Montepulciano.
Cortona was already old by the time Rome existed. It was one of the twelve cities of the ancient Etruscan League, likely founded in the 8th or 9th century BC, and the Etruscan "cyclopean" walls that once enclosed a town far larger than today's Cortona are still partly visible on the hillside. The town's museum holds one of the most important Etruscan collections in Italy — a deep layer of history easy to miss beneath Cortona's better-known modern reputation.
That modern reputation comes almost entirely from one book: Frances Mayes' 1996 memoir "Under the Tuscan Sun," and the 2003 film adaptation starring Diane Lane, introduced Cortona to English-speaking travelers in a way nothing else had before. Mayes still keeps a home in town, and the connection is a genuine part of why Cortona draws visitors today, not just marketing.
Montepulciano's own history runs deep in a different direction: a document from 789 AD records a gift of vineyard land to the local church of San Silvestro, making it one of the oldest continuously documented winemaking sites in Tuscany. Vino Nobile di Montepulciano, the wine made there today, became the first Tuscan wine ever awarded DOCG status — Italy's highest quality classification — in 1980, and the medieval streets around Piazza Grande, with its 14th-century town hall and 17th-century cathedral, are built around that same winemaking tradition.
Every Voyzo tour is a starting point — tell us what you have in mind and we'll build it.
