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Exploring the Italian countryside by train is certainly no snore, but imagine cruising Italys hilltop villages, cliff-hugging highways, and rolling vineyards in your own convertible 1974 Alfa Romeo Spider or 1964 Lancia Flaminia GT. Italy by Vintage Car makes it doable with perk-packed auto excursions that include stays at prime hotels, such as Borgo la Bagnaia in Siena or Villa Spalletti Trivelli in Rome. The price covers hotels, meals, fuel, full insurance, and a valet-mechanic who washes, gasses, and parks the car each night. The company offers six itineraries, including Tuscany, the Amalfi Coast, and Rome to Milan. From $4,890/person for two nights, based on two people sharing a room and car.