The Arezzo area is one of the oldest wine-producing regions in Tuscany thanks to Cosimo III’s edict in 1716. Many of the wineries follow the Valdarno di Sopra DOC production guidelines, where international varieties like Merlot and Chardonnay sit comfortably alongside local grapes such as Sangiovese and Malvasia Bianca. Our first stop is Il Borro, an all-organic luxury estate 20 minutes southeast from Loro Ciuffenna by car. Owned by the Ferragamo family, stroll over the medieval bridge and up the hill to the spotless village dotted with artisan stores and first-rate holiday apartments. Enjoy a tasting in the centuries-old cellars after admiring the collection of etchings and paintings in the Wines&Art Gallery. Next up is Tenuta San Jacopo, southwest of Loro Ciuffenna on the border between the Valdarno and Chianti. The mostly organic wines from this beautiful estate reflect the location, ranging from Chianti DOCG to an unusual Chardonnay, Pinot Nero and Sangiovese sparkler. Both of these estates offer opportunities to experience the grape harvest from early September to late October.