Medieval UNESCO-listed San Gimignano has 14 lofty square towers which combine to create a striking skyline that can be seen framing the surrounding hills from miles away. Visit the Torre Grossa tower, Palazzo Comunale, Piazza della Cisterna and the Cathedral of San Gimignano. Rich in works of art, spectacular piazzas, fine shops and vibrant restaurants, San Gimignano’s serenity and beauty have made this place one of the most popular destinations in Tuscany.
The Chianti region, made famous by the wine of the same name, is dotted with historic cities, towns and villages, including the riverside city of Gaiole which is surrounded by striking castles and churches. Wine tasting is a must (make sure to book ahead) as is a visit to the doorway of Chianti, Greve, and the immense castle and underground series of roads in Castellina.
Located in the heart of Tuscany, Siena is one of Italy’s best-preserved medieval towns filled with fine examples of Gothic architecture. If you’re visiting during July or August then don’t miss the chance to attend the Palio in Siena – the most famous bareback horserace in history – where the riders and their steeds strut past the crowds in colourful finery.
Where is Rural Tuscany
The hilly areas of central Italy’s Tuscany are what define rural Tuscany, with the Valdelsa area near Florence and the Chianti hills extending from Siena to Arezzo and on to the Tiber Valley.
We recommend hiring a car to make the most of exploring the region as scenic drives take you to smaller towns and villages and enable you to reach the hidden corners of rural Tuscany. Parking can be difficult and driving is not allowed in historic centres, so we advise parking outside the city limits and either walking or catching a bus into villages and towns.
Food & drink
Enotecas and restaurant menus are packed with local specialities and you’ll find plenty of wood oven pizzerias and cafés inside the hilltop town’s central piazzas. Pore over extensive wine lists in al fresco restaurants. Dine in the middle of the Chianti hills with panoramic views and in medieval vaults under the Duomo in Siena. Try handmade rolled spaghetti, Tuscan bread and tomato salads and pici in rabbit sauce.
GMT +1 hour
2 hours to Pisa