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Milan, Italy
Start your journey in Italy's fashion capital. Don't miss Leonardo da Vinci's Last Supper (book well in advance) and explore the vibrant Navigli canal district for aperitivo and dinner.
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Venice, Italy
Park your car at Piazzale Roma or Mestre, as the historic center is car-free. Wander beyond St. Mark's Square into the quieter Cannaregio and Dorsoduro neighborhoods, and try fresh cicchetti at a local bacaro.
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Florence, Italy
The cradle of the Renaissance is home to the Uffizi Gallery and Michelangelo's David — book tickets ahead. Climb to Piazzale Michelangelo at sunset for a stunning panorama and grab a bistecca alla Fiorentina for dinner.
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Siena, Italy
A gorgeous medieval hill town with one of Italy's most beautiful squares, Piazza del Campo. Explore the striped Siena Cathedral and sample the local pici pasta with wild boar ragù.
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Rome, Italy
The Eternal City deserves several days — the Colosseum, Vatican Museums, and Trastevere neighborhood are unmissable. Toss a coin in the Trevi Fountain and fuel up on supplì and cacio e pepe in a local trattoria.
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Naples, Italy
Naples is loud, chaotic, and utterly captivating — birthplace of pizza, with Pompeii just a short drive away. Explore the underground Spaccanapoli district and eat the best margherita of your life at a historic pizzeria.
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Palermo, Italy
Take a ferry to Sicily and end your road trip in Palermo's vibrant street markets like Ballarò and Vucciria. Arab-Norman architecture, arancini, and cannoli make this city a spectacular finale to your Italian journey.