Built in 1361, Montalcino’s dramatic 5-sided fortress encloses a cobbled courtyard and chapel, and is topped by crenelated ramparts and soaring towers. Explore the fortress on a wine tour from Florence, Rome, or Siena: take in the views over the vineyards and olive groves of the Val d’Orcia and sit down for a tasting of local Brunello wines in the cellar wine shop. Most wine-tasting day trips stop in a number of picturesque villages that dot Tuscany’s wine country—including Montepulciano, Pienza, and San Gimignano—and include lunch featuring Tuscany’s famed cuisine.