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Milan, Italy
Start your road trip in fashion-forward Milan — visit the stunning Duomo and the Navigli canal district for aperitivo hour. Don't miss a risotto alla Milanese or a panzerotto from Luini. Great base to pick up your rental car and hit the road.
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Cinque Terre, Italy
Five colorful clifftop villages along the Ligurian coast — hike between them or hop the local ferry for stunning views. Feast on fresh focaccia, pesto pasta, and grilled seafood straight from the harbor. Swimming stops and boat rentals make this a perfect activity-packed stop for three.
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Florence, Italy
Florence is a paradise for food lovers and culture seekers — explore the Mercato Centrale for local cheeses, meats, and lampredotto sandwiches. Book a Tuscan cooking class together for a hands-on group activity. Walk across the Ponte Vecchio at sunset and explore the Uffizi Gallery.
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Rome, Italy
The Eternal City deserves extra time — toss coins in the Trevi Fountain, explore the Colosseum, and get lost in Trastevere's maze of trattorias. Eat cacio e pepe and carbonara at a proper Roman osteria, then finish with gelato near the Pantheon. Book a Vatican tour early to skip the queues.
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Naples, Italy
Naples is the birthplace of pizza — grab a Margherita at Da Michele or Sorbillo and prepare to be changed forever. The chaotic energy of the city is thrilling, and a day trip to Pompeii or the Amalfi Coast is a must-do for the group. Don't leave without trying a sfogliatella pastry and some fried street food from Spaccanapoli.
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Palermo, Italy
End the road trip in Sicily's vibrant capital with a street food tour through Ballarò market — try arancini, panelle, and cannoli fresh from the fryer. The Arab-Norman architecture and the stunning Palatine Chapel are highlights not to miss. Catch a ferry or fly back from Palermo to wrap up the ultimate Italian adventure.