Tenuta Guardastelle San Gimignano


The Territory around San Gimignano

During your stay on the estate you will have the unique opportunity to walk into San Gimignano, avoiding the hassle of having to find a parking space (always scarce and expensive).

Guardastelle is linked to San Gimignano by the Via Vecchia which, as its name suggests, is the old road. It is still unpaved but is a very pleasant walk from which you can enjoy a unique view. It takes about 20 minutes to reach the village, walking past cultivated fields and other farms. May and June are definitely the best months to appreciate one of nature’s wonders: thousands of fireflies twinkling in the fields will light up the way back, making you feel as though you are in a fairy tale!

Valori Tenuta Guardastelle San Gimignano

San Gimignano

The atmosphere in San Gimignano will also offer you a timeless experience, as the town, the surrounding area and its agricultural production are as old as humanity. The first documented settlements date back to the Etruscan period. Despite its ancient origins, the golden age of San Gimignano, also known as the Manhattan of the Middle Ages, was between the 10th and 14th centuries.


Just a 20-minute drive away and, like most of the little villages in this area, the origins of the first settlement of Certaldo date back to Etruscan times. However, it was in the 14th century that the town became an important literary centre, giving birth to one of the most famous writers of his time: Giovanni Boccaccio. Today you can visit his home and many other historical and cultural sites, as well as excellent restaurants, and go for walks in the Canonica park.


Visitors to Volterra will find medieval buildings, Etruscan origins and Roman ruins. A wonderfully preserved village, encircled by walls and surrounded by breathtaking views of hills covered with cereal crops.

The charm of this little village will take you back in time. It lies about a 40-minute drive from the estate; we recommend visiting it by public transport.


Torre del Mangia, Piazza del Campo, the Palio and the marvellous Cathedral with its works of art of inestimable value and importance, including some sculptures by Michelangelo. It would take hours to describe Siena, so we recommend a guided tour. It lies about a 40-minute drive from the estate and is also easily reached by bus.


The city of flowers is the original name of Tuscany's most important city. No end of museums and works of art that would take weeks to visit: Palazzo Pitti, the Bargello, Palazzo della Signoria, Ponte Vecchio, the Uffizi Gallery and Accademia museum, the Cathedral and Giotto's bell tower are just the most famous. Easily accessible by train or bus; Fausto comes from Florence and can advise you on the best and least stressful route to the city by car.

Pisa and Lucca

An extremely important maritime city since ancient times, it is now famous and visited mainly for its well-known tower. Combining a visit to Pisa with a visit to the city of Lucca and its impressive walls, or spending a few hours on the beach in Vecchiano, is an excellent idea. It lies just over an hour’s drive from the estate.


A hydraulic system used to power mills and other artisan activities for many centuries; restored by the Grand Duke of Tuscany in the 17th century, it is now a trail of about 4 km where one can spend the day cooling off from the summer heat. There is a river where you can swim just 15 minutes from the estate. We can advise you on the best place to park your car.

Chianti Classico

Usually referred to simply as Chianti, this is the central part of this region that is internationally famous for the wine made here, mainly from Sangiovese grapes. The little villages in this area are all delightful and well worth a visit. You may decide to do some wine tasting along the roads of Chianti Classico. We will try to suggest some non-commercial wine cellars for your experience.


A little Medieval town which was often the scene of clashes between the provinces of Siena and Florence, Montalcino is now a splendid town famed above all for its most prestigious wine: Brunello di Montalcino. Full of restaurants and narrow streets, it will be a pleasure to wander along its lanes to discover the most stunning views.