A soaring Gothic cityscape, warren of medieval cobblestone alleys, and raucous annual Palio horse race make UNESCO-listed Siena a Tuscan A-lister. Visitors can marvel at its open-air museum of a historic center—thick with architectural masterpieces like the Piazza del Campo and Duomo—and soak up the authentic vibe of the contrade neighborhoods. Set in the heart of Chianti, Siena is also a popular departure point for countryside wine tours and cooking classes, outings on horseback or Vespa scooter, hot air balloon adventures, and hill town hopping between Pienza, Montepulciano, Montalcino, and San Gimignano.