As one can imagine, the wine making history in Tuscany goes back thousands of years. By thousands, we mean pre-Romans, all the way back to the Etruscans, like 500 B.C.! Truly a defining old world region, Tuscany is home to the Chianti, Chianti Classico, Brunello di Montalcino and Vino Nobile di Montepulciano appellations. Spanning nearly 9,000 square miles from the northwestern coast along the Tyrrhenian Sea running south to the central heart of the country, it is the fifth largest wine region in Italy.