Welcome to the Manhattan of the Middle Ages

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 (12th – 1st century B.C.). 

In Roman times, the castle was named Silvia and the first official document with the current name of San Gimignano dates back to 929 AD. It seems, however, that the town was already referred to by this name in the mid-5th century.

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, as it was strategically located. It was the crossroads between the most important Tuscan cities of Florence and Siena as well as one of the major stops along the route of the Via Francigena, all of which allowed the small town to become a rich trading centre as early as the Middle Ages.

Local products that were already appreciated in ancient times were saffron, used to dye textiles but even more importantly as currency to pay mercenaries (in the mid-13th century) or to finance the construction of the family tower, as well as being used in medicine and ultimately, in the present day, as a prized ingredient in cooking.

Wine. The subject of wine is so vast that it is quite easy to get lost, so let’s stick to the specifics of what are currently the two most important appellations of San Gimignano: Chianti, particularly the Chianti Colli Senesi subzone, and Vernaccia di San Gimignano both of which are produced in small quantities but with great pride at Tenuta Guardastelle, a small family-run winery in Tuscany.

San Gimignano is a small town in the heart of Tuscany that offers numerous experiences:

• wine tastings at the wineries
• hot-air balloon flights
• tours of the vineyards of Vernaccia di San Gimignano
• walks in the Castelvecchio Nature Reserve
• visits to the museums of San Gimignano
• guided tours of the old town
• the possibility to climb a tower built in the Middle Ages
• the chance to eat one of the world’s most famous ice creams
• relaxing days by the pool
• eating in a Michelin-starred restaurant
• visits to an oil mill
• swimming in a turquoise river
• visits to natural thermal baths
• a day at the spa.

Many other towns are just a few minutes’ drive from our estate, but, above all, the cities of Siena and Florence can be visited on a day trip. Our guests often leave after breakfast for an unforgettable sightseeing tour of the city and return late in the afternoon, just in time for an aperitif on the estate and a refreshing dip in the pool.