2Tuscany Wine Country

Tuscany’s vineyard-dotted landscape makes for the quintessential Italian road trip.

Start in Florence and cruise south on the SS22 for 30 minutes until you reach the heart of the Chianti wine region.

Where to stop: Ruffino’s sprawling Poggio Casciano estate for truffle hunting and tasting; Antinori nel Chianti Classico for its Instagram-worthy glass-and-steel winery and equally show-stopping wine; Tenuta Il Greppo, where the first Brunello di Montalcino was bottled in 1888.

Where to eat: Officina della Bistecca in Panzano-in-Chianti for the best steak in all of Tuscany; Re di Macchia in Montalcino for its classic, hearty Tuscan cuisine like white bean soup and wild boar pasta.
Where to stay: In castles, always. We like the intimate, art-filled Castello di Ama in Gaiole in Chianti and the lavish, hilltop Castello Banfi il Borgo in Montalcino, which has an infinity pool overlooking the vineyards. Click the next ARROW to see the next image!