There are many reasons for Tuscany’s enduring appeal. One is the more than 2,000 years of history, which has left a mark on the landscape and the people, from the Etruscans through the Medicis to today’s wine and fashion dynasties. Another is the region’s civility. Whether it’s the placement of a cypress on a hill, a bruschetta drizzled with just-pressed olive oil, the cut of a Florentine shoemaker’s brogue or the radiant grace of a fresco by Masaccio, Tuscans seem to take pride in living life as if it were a form of art. (Read about the exhibit "Americans in Florence: Sargent and the American Impressionists"—a showcase of Florence as seen through the eyes of the painters who came to the city in the late 19th century, on view at Fondazione Palazzo Strozzi—here.)
When it comes to deciding which villa to rent, it’s easy to get lost in the maze of possibilities. The recommendations are so profuse—one friend says this, another that, while agents try to make their inventory so comprehensive, all they create is confusion. Which is why we have sifted through dozens of properties in order to select ten of the best. Our short list comprises not necessarily the most expensive or luxurious villas, nor are they all in the deeply sculpted and panoramic Val d’Orcia, Tuscany’s super-fashionable heartland. Rather, we have looked farther afield, to the southern Tuscan coast, and delved deep into classic Chiantishire (so named for the number of seasonal British residents in these pretty wooded parts), and at the end of our endeavors, we are left with no doubt that the villa tradition is one that works best in this part of the world. After all, it is a mode that’s older than the Medicis—even if not all the great houses adhere to Lorenzo’s classic cut, but, instead, are modern, surprising and, on occasion, stuffed with contemporary art.