Chianti Vineyards
The gentle hills and valleys of Chianti sit snugly between the great art cities of Siena and Florence and are host to some of Italy’s best vineyards. Forests of oak give way to open pasture, while easy country roads lead to remote abbeys and hilltop castles. This is an area for the meandering drive and the curious traveller. Morning markets in vibrant piazzas, picnic lunches with the best local produce and wine tasting in ancient cellars are what Chianti is all about. With no big towns to speak of, it is one large glorious garden to wander through at leisure.
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ACTIVITIES
Swap the car for a bike and pedal past olive groves and vineyards on quiet country roads
Follow in the footsteps of Benedictine monks and take a walk up the Arno Valley by the Badia a Coltibuono
Stock up on “La Cinta Senese” sausages, made from the local breed of swine, at a famous butcher’s in Panzano
Be a barone for a day and sup from the world-class cellars of several castles-turned-wineries
Traditional straw-covered, rounded Chianti fiaschi (flasks) stored on an old cart in a vineyard at Villa a Sesta
PLAN YOUR DRIVE
Start/finish: Siena to San Casciano.
Number of days: 3, allowing for a half day in Siena and a half day’s side trip to San Gimignano.
Distance: 134 km (83 miles). Siena to Castellina 66 km (41 miles); side trip to San Gimignano 28 km (17 miles); Castellina to San Casciano 40 km (25 miles).
Road conditions: Mostly on well-maintained provincial roads. Be wary in rain or snow on smaller “white roads.”
When to go: Spring and autumn are the best times, especially late autumn when leaf colour can be exceptional.
Opening times: Most museums open 9am–7pm and often close Mon and Sun afternoon, with shorter hours in winter. Churches can be unpredictable, and usually close noon–3 or 4pm.
Wine estate tours & tastings: Vineyards in the Chianti are working enterprises so it is best to book in advance for tours and tastings, though large operators such as Castello di Brolio are well staffed. Look out for hand-painted “Cantina Aperta” signs, which indicate that the smaller vineyards are open for tastings and purchases. Expect a charge of around €10–20 for a tour and tasting. Snacks or nibbles are often included.
Main market days: Gaiole: 2nd Mon; Radda: 4th Mon; San Gimignano: Thu; Greve: Sat.
Major festivals: Siena: Palio horse race, Jul 2nd & Aug 16th; San Gimignano: Medieval Festival, 2nd weekend Jun; Chianti: Classico Wine Festival, 2nd weekend Sep; Greve: harvest festivals across Chianti Sep/Oct.
The medieval towers of San Gimignano rising high above the hilltop town.
DAY TRIP OPTIONS
The tour is easily treated as a series of day trips. Art and history enthusiasts can combine Siena with the castles of Chianti; keen photographers should not miss the skyline of San Gimignano; and visiting the vineyards around Greve is a must for wine buffs – for full details see Day trip options.
Villa Vignamaggio, ancestral home of (Mona) Lisa Gherardini, with the family coat of arms above the door.