Where to start? In Florence, don’t miss the Uffizi for the paintings, the Accademia for Michelangelo’s David, and fresco-laden churches like Santa Croce and Santa Maria Novella, capped off by a stroll along the Arno and across the Ponte Vecchio bridge. In Pisa, the Leaning Tower (or simply, “The Tower”) is a must for the photo ops, while Siena’s central Piazza del Campo—home to the Gothic Palazzo Pubblico and a 14th-century tower, and surrounded by the brick-faced historic center—is a visitor favorite. Day trips to medieval hill towns like San Gimignano, Volterra, and Montalcino add plenty of charm and authentic flavor—especially in Pienza, famous for cheese, and Montalcino, home of Brunello wine. Don’t leave without a visit to a vineyard and, if the sun’s out, a stroll along the beach at Forte dei Marmi or Viareggio.