Do you think there’s a connection between the beauty of a territory and the quality of its wines? In Tuscany, definitely. This region’s wines are part of a long winemaking tradition that originated with the Etruscans and still continues to innovate, leading to the creation of true oenological treasures. Along the roads running beside the rows of vines that disappear into the green, winding hills, there is always a castle, an abbey or a village to visit that will delight you with the local wine produced there: of these, Bolgheri and San Gimignano are two destinations not to be missed.

Viale dei Cipressi, Bolgheri
Bolgheri: an ancient village with a recent history
Taking the long and scenic Viale di Cipressi, which stretches for 5 km from the historic Tenuta San Guido to the gateway of Bolgheri, you’ll pass the neat vineyards that are the lifeblood of some of the world’s most renowned labels: Sassicaia, but also Ornellaia, Masseto, Messorio, Grattamacco and many others: names that are sweet music to the ears of wine connoisseurs. Here, the intoxicating beauty of the land revolves entirely around wine. Although the village has medieval origins, its wine-growing tradition belongs is relatively recent and was initiated by the Piedmontese, Mario Incisa della Rocchetta who created a legendary wine: the Sassicaia. Since the first vintage went on the market in was 1968, the name of Bolgheri has made its way onto the map of world-class wines and frontrunner of one of the latest revolutions in Italian wine.
Refined, rich, Mediterranean reds

Valued for their longevity and refinement, deeply evocative of fruit and spices on the nose and palate, Bolgheri wines capture in the glass what the French call terroir, that is the sense of place made from the blend of various factors: climate, soils and traditions. Produced in an area between the sea and hills, Bolgheri DOC (Denomination of Controlled Origin) wines are mainly reds made from international grapes such as Cabernet Sauvignon, Merlot and Cabernet Franc, the varieties that have made Bordeaux wines so famous, but here it is the strong Mediterranean influence of the that makes the difference. If instead you prefer white wines, there are varieties such as Vermentino and Viognier, which are equally distinctive and pleasing.
San Gimignano: vineyards in the shadow of the towers

Vigneti intorno a San Gimignano
Expanses of tremulous olive groves interspersed with neat rows of vines provide the perfect setting for one of the world’s most famous skylines: that of San Gimignano. In contrast to Bolgheri, San Gimignano has been famous for its wines sold in taverns from Siena to Florence since medieval times. Overlooked by the tall and slender towers, the Vernaccia, a native white grape, has made Tuscan wine history.
Vernaccia, a precious white among the Tuscan reds
Elegant and lofty like the city’s towers, yet also fresh and delicately fruity: the Vernaccia di San Gimignano is famous for being an outstanding white among so many renowned red wines and for being the first Italian wine to gain the DOC classification in 1966, updated in 1993 to a DOCG (Controlled and guaranteed designation of origin).
Where to find and taste Bolgheri wines
An excellent way to discover and understand a wine is to walk through the vineyards, descend into the hallowed darkness of the cellars where the wine is produced and aged, and then conclude with a well-deserved tasting. Most wine estates offer tours – pre-booking essential – depending on their availability and the selection of wines, like that at Michele Satta or the Chiappini winery, which takes around 2 hours. Otherwise, as an experience for the whole family the Guado al Melo winery offers an itinerary that includes the underground cellar, constructed on the principles of bio-architecture, which also houses a museum and one of the largest libraries on the culture of wine in the world.
Outside the wineries…
There are also wine shops and restaurants where you can get to know the famous wines of Bolgheri. In the centre of the village, the Tognoni wine shop is a must for wine tourists, or book a table at the Osteria Enoteca San Guido for an encounter with the legendary Sassicaia. In a typical Tuscan farmhouse along the Via Bolgherese, the Osteria Magona offers a combination of fine local wines with renowned local dishes: from cold cuts to the bistecca alla fiorentina, this is a great place to savour the finest Tuscan meats.
Where to find and taste Vernaccia di San Gimignano
The Vernaccia is the pride of San Gimignano, it has its own space on the Rocca di Montestaffoli, the highest and most central point of the city. It is more than just a wine, it’s a journey through Tuscan history, scents and flavours. There are several wine-tasting options at the Vernaccia di San Gimignano Wine Experience, but if you prefer to explore just one winery, Panizzi, which, in addition to the wine, has an excellent extra virgin olive oil, while at Guicciardini Strozzi there’s another local delicacy on offer – the truffle – along with a tour of the historic cellars and the beautiful and memorable Renaissance gardens.