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Rome, Italy
Start your trip in the Eternal City — visit the Colosseum, Vatican Museums, and wander Trastevere in the evenings. May is ideal with warm weather and fewer crowds than summer. Don't miss supplì (fried rice balls) and cacio e pepe pasta.
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Florence, Italy
Florence is compact and walkable — book the Uffizi Gallery and Accademia (Michelangelo's David) in advance. Climb the Duomo's dome for panoramic views over the city. Cross the Ponte Vecchio and explore the Oltrarno neighbourhood for local trattorias.
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Bologna, Italy
Bologna is Italy's food capital — try authentic ragù, mortadella, and tortellini in brodo at the Mercato di Mezzo. Climb the Due Torri (Two Towers) for great views over the terracotta rooftops. The portico-lined streets make it a perfect city to explore on foot.
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Cortina d'Ampezzo, Italy
The gateway to the Dolomites, Cortina is stunning in May with snow-capped peaks and blooming alpine meadows. Take cable cars up to Tofane or hike trails around Lago di Misurina for dramatic scenery. The town itself has great mountain restaurants serving hearty dishes like canederli and speck.