The origins of Castello Vicchiomaggio can be traced back to the beginning of the15th century; majestically positioned on a hill top dominating the Greve Valley between Florence and Sienna, it has played a significant role in the region’s history. During the Middle Ages, the castle was crucial for the defence of Florence during its feuds with the city of Siena. Later it played its part in the Renaissance period when its original name was changed from Vicchio dei Longobardi to Castello Vicchiomaggio with the addition of the word Maggio (May). The Castle has hosted various famous artists, including Leonardo da Vinci and Francesco Redi; Leonardo stayed at the castle at around the same time he painted the Mona Lisa.

In 1964 the Matta family purchased the property and then restored it back to its former splendour. The estate, of about 150 hectares, is one of the largest in the area, there are 32 hectares of vineyards. The present estate owners, John and Paola Matta, are very keen on preserving the winemaking traditions of Vicchiomaggio to produce high-quality wines; traditional processes only give way to modern, innovative techniques if there is a proven benefit. John takes the role of winemaker at Castello Vicchiomaggio; his wines always show elegance and style and are all beautifully balanced. Vicchiomaggio is consistently classified amongst Italy's top estates and John Matta has been named Italian Winemaker of the Year at the International Wine and Spirit Competition four times in the last two decades (1997, 2002, 2005 and 2010). All the vineyards are strictly classified according to typology and exposure and each wine is labelled after the name of its original vineyard.