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Rome, Tuscany, Venice, the Italian Riviera, and the Amalfi finish. Trains between cities, no car until the south.
Build this tripDays 1-3 Rome: Colosseum, Vatican, Trastevere evenings. Day 4 high-speed train to Florence (1h30m). Days 4-6 Florence: Uffizi, Duomo, day trip to Siena or San Gimignano. Day 7 train to Cinque Terre (3h). Days 7-8 Cinque Terre: hike between the five villages, swim. Day 9 train to Venice (6h -- or fly Florence-Venice 1h). Days 9-11 Venice: St Mark's, Dorsoduro, Burano day trip. Day 12 train/flight to Naples, rent a car. Days 12-14 Amalfi Coast: Positano, Ravello, a Pompeii half-day. Fly home from Naples.
May or September-October.