Villa Holidays In Chianti & South Of Siena

Chianti’s vine-clad fields, hill towns, and wine and olive groves offer a “classic Tuscany” while Siena has Medieval art to boot.

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Chianti and South of Siena holiday guide

The hills south of Florence, known as the Chianti, look like most people’s idea of ‘classic Tuscany’. Fortress towns such as Castellina and Radda look out over mile after mile of rolling, vine-clad fields, spotted with Tuscany villas. The region’s major annual festival, September’s Rassegna del Chianti Classico in Greve, celebrates the grape harvest, and signs inviting anyone on a Chianti holiday to a roadside enoteca (wine tasting cellar or shop) are a common sight. The Gothic city of Siena, south of Chianti, is the biggest hill-town of all, with a stash of Medieval art and architecture unmatched in Italy.

But Tuscany still has surprises to offer, and unknown even to many Italians. Maremma, only a two-hour drive southwest of the city of Florence is an extensive and largely undeveloped territory in stark contrast to the compact, ordered Chianti hillsides around Florence and Siena that have, until now, been the major draw for visiting wine lovers.The Maremma has great restaurants, and a treasure trove of new wineries.

Our Chianti and South of Siena Villas