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Chianti in the heart of Tuscany represents what most travellers consider to be the essence of Tuscany. An area of rolling hills, patchwork farms and lovely forests interrupted by authentic Italian villages, hilltop castles and delicious Chianti wines. Situated on the eastern side of the road between Florence and Siena it is a wonderful base for exploring Tuscany.

Why Chianti

  • Centrally located near major cities and motorway
  • Beautiful countryside and wines
  • Wonderful selection of accommodation


San Casciano Val di Pesa, on the northern edge of the Chianti Classico zone, is the first major town on the Chiantigiana route from Florence. It is also the largets town (pop.16,000) in the area. Parts of the 14th century walls still remain, and the town is home to an interesting church, Santa Maria del Prato, housing works by Simone Martini, Ugolino di Neri, Taddeo Gaddi and Fra Bartolomeo.

, the chief town of the Gallo Nero region, is home to Chianti's largest wine fair, held every September. The small village, named after the nearby river, expanded considerably during the 14th & 15th centuries, and, after the unification of Italy, became the most important centre of the valley.
Today you will find a wine shop around every bend, with some of the better ones being found in the Piazza Matteotti.

Castellina in Chianti
is another quietly affluent hilltop town, yet it was at one time at the very frontline of the ebbing and flowing wars between Florence and Siena. A striking remnant of those times is the Via delle Volte, a covered gallery that was once part of the town fortifications. The old fort, in the central square, is now home to municipial offices.

Radda in Chianti
, to the east of the Chiantigiana route, has retained more of its ancient character than most towns and villages of the area. It is located in the hills of Chianti, the Monti del Chianti, and was once the seat of the mediaeval Lega di Chianti. This once powerful league placed the black cockerel, the Gallo Nero on all bottles of Chianti, as its symbol.

Accommodation options that we can offer in Chianti include independent rental villas and holiday apartments, often situated amongst the rolling hills or forests, “agriturismi” or working farms that are often found in working vineyards (under B&Bs). In each of our properties, you will find a book of local advice and tips regarding local secrets, discoveries, restaurants etc.

Villa rental holidays in Chianti, Tuscany.
Browse our selection of villas and self-catering accommodation for rent in Chianti or a nearby locality in Italy. Our office staff have first hand knowledge of the areas and villas and are supported by our network of local area managers present during your vacation.

Things To Do in the Chianti Locality (coming soon)

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