Italy: Tuscany

Between San Gimignano and Siena

Chianti Classico, San Gimignano and some Super Tuscans
By Michèle Shah

This Guide was last updated on 30 March 2010
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Main towns and villages


Siena is a place you must visit, whether for culture or shopping: it is one of Tuscany’s gems. If it is shopping you are after you have an array of fashionable shops in the crowded Via dei Banchi di Sopra, which takes you from Piazza Salimbeni right down to the shell-shaped Piazza del Campo, the heart of Siena. Visit the Palazzo Pubblico, which houses the Civic Museum including Ambrogio Lorenzetti's series of frescoes Effects of Good and Bad Government, and also some of the finest frescoes by Simone Martini. If you have the energy, climb the Torre del Mangia, attached to the Palazzo Pubblico, which offers incredible views of the countryside around Siena. Another must is Siena’s 12th-century Duomo with its intricately carved marble façade.

Castellina in Chianti

Castellina’s history clearly dates back to the Roman times and evidence of its roots can be seen in the burial vault of Montecalvario, which measures about 53 metres across, discovered just outside the town on the road to Florence. During the Middle Ages, Castellina played a military role within the Chianti Alliance mainly because of its strategic location, which guaranteed the control of all the surrounding roads as well as the entire valley. Evidence of the town’s importance during this period is its imposing fortress on the main square. At this time the entire town was surrounded by massive defensive walls and towers, with only two gates providing access, one towards Siena, the other facing Florence. Though both gates were completely destroyed, most of the walls still stand today. Castellina has some good local trattorias and enoteca wine bars to visit.  Also be sure to visit the wine museum on the main street, you can’t miss it!  It houses a fine collection of historic bottles of Chianti Classico – some are for sale as collector’s items.

Radda in Chianti

Radda in Chianti was originally the capital of the Chianti League villages and is located between the valleys of the rivers Pesa and Arbia, surrounded by extensive vineyards leading towards gentle hills dotted with castles and farms. The village of Radda in Chianti provides a number of enoteca wine bars, restaurants and shops for visitors. Take a stroll down the main street to soak in the atmosphere of local colour. There are numerous excellent agriturismi within easy reach of Radda, providing reliable vacation accommodation. There is no better way to enjoy the ambience of Tuscany than to stay in a Bed and Breakfast, farmhouse apartment or villa on a working Tuscany vineyard.

Panzano in Chianti

Panzano in Chianti is located on a high ridge on the scenic Via Chiantigiana (SS 222), exactly halfway between Florence and Sienna. It is a charming small town with some characteristic artisanal shops, trattorias and a wine bar on the main square – be sure to pay a visit to Dario Cedcchini’s butcher shop or restaurant.  There is one main street leading to the church of Santa Maria which was completely renovated a century ago. It has a late Gothic Madonna and Child attributed to Bernardo di Stefano Rosselli encased in a larger picture with saints and angels. In the nearby oratory is an Annunciation attributed to Michele di Ridolfo del Ghirlandaio.

San Gimignano

A UNESCO World Heritage site, San Gimignano is known for its many towers, which stood tall during the Middle Ages and the Renaissance era. At that time it was a rich merchant city and a stopping point for Catholic pilgrims on their way to Rome and the Vatican, as it sits on the medieval Via Francigena . The heart of the town contains four very picturesque squares – Piazza della Cisterna, Piazza Duomo, Piazza Pecori and Piazza dell’Erbe. The main streets are Via San Matteo and Via San Giovanni, which cross the city from north to south. Be sure to visit the Communal Palace, once the seat of the Podestà, which today is home to the Town Gallery showing Renaissance masterpieces. Also well worth visiting is the Collegiata, located in Piazza Duomo, which houses a famous cycle of Benozzo Gozzoli’s frescoes.

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