All roads may lead to Rome, but we know the scenic avenues to reach all the enchanting cities on your Italy bucket list. That serene passageway in Assisi, that chic leather boutique in Florence, that off-the-beaten-path bridge in Venice—we know the way! We’ve mapped out the iconic experiences of Italy, leading you through the historic streets and piazzas of the “Eternal City,” the vine and olive-clad hills of Tuscany, and the romantic canals of the “Floating City” so you can experience the art, architecture, vino, and espresso you’ve long imagined. On this dreamy tour of Italy’s great cities, you’ll wake up to lush gardens in San Martino in Campo, stroll through the medieval-walled city of Siena, ponder the curious tilt at the Tower of Pisa, and happily tuck into the delicious plates of pasta, pizza, and pastries along the way.