A millennium ago, Rome-bound pilgrims cut across Tuscany on the Via Francigena trade route, passing through Florence, San Gimignano, and Siena by foot. Now you can retrace some of their tracks on the country's emblematic two-wheeler. Starting next month, Italy by Vespa, a travel company associated with Vespa manufacturer Piaggio, will be running scooter trips through the Tuscan countryside . Guests receive driving lessons on ruby-red Vespas, use of a helmet, a half-day cooking class, and insurance. Pit stops include the medieval hamlet of Monteriggioni, a wine tasting at Chianti's up-and-coming Dievole estate, the Prada outlet near Montevarchi, and Ferragamo's private village. Each day ends in Radda at the luxe Palazzo Leopoldo hotel and spa. 866/297-7725 or 303/669-5237; www.italybyvespa.com; one-week trips from $3,895 per person, airfare not included.