This packed 5-day itinerary is perfect for travelers with a thirst for adventure who are on a time crunch. Explore the glass-roofed Galleria Umberto shopping center, enjoy coffee on the medieval Piazza del Plebiscito, and try the seafood cuoppo in Naples. Visit the Pompeii ruins, hike around Mt. Vesuvius, and visit colorful bohemian Positano on the Amalfi Coast. Make sure you try the Naples pizza—the Amalfi Coast's real highlight.
Italy 5-Day Tours & Itineraries
For more ideas, see 5 Days in Italy - 5 Unique Itinerary Ideas.
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Spend five days exploring the art and cuisine of Italy's Tuscany region. Discover Rennaissance art in Florence, browse bustling markets for fresh produce and cured meats and stroll through narrow medieval streets to see the 1,000-year-old Ponte Vecchio bridge. Head to the Tuscan countryside to visit Siena, tour a typical Chianti winery, and see the medieval Monteriggioni fortress. End your visit with a trip to see the famous leaning tower of Pisa and Lucca's historic city walls.
Discover historic and modern highlights of the Eternal City in this 5-day tour. Hear stories of gladiators in Rome's ancient Colosseum, tour the iconic Pantheon and visit the Vatican Museum to see the world-famous Sistine Chapel. Explore the Galleria Borghese to see works by Rafaello and Caravaggio, then stroll around the peaceful gardens of Villa Borghese. Enjoy a quiet cup of coffee in the Piazza Navona and unwind at night with a homemade Italian pizza and a glass of wine.
Explore Northern Italy's cities and landscapes in this packed 5-day trip. Start in Milan, the fashion, culture, and business capital of Italy, to see the 16th-century Royal Palace-turned-art-museum and enjoy buzzing nightlife at the Navigli canals. Continue to Lake Como to enjoy a day on the lake and a trip on the funicular to see views of the snow-capped Alps. End in Bologna and Turin to explore medieval churches, the National Cinema Museum, and endless cafes and aperitivo bars.
Take a quick spin through the birthplace of the Italian Renaissance with this five-day Tuscan cycling tour. This challenging bike route will take you through the medieval villages and cypress-spotted hills of the Tuscan wine region . Go from Florence to Siena as you take in the region's food, historic castles, and sun-kissed landscapes, accompanied, of course, by a good glass or two.
Explore western Sicily on this 5-day trip, from cultural Palermo to sunny Cefalu. You'll see medieval churches, tour the macabre Caphucin Catacombs, and soak in the sunshine on Cefalu's beaches. From the hustle and bustle of the street markets to the quiet of the Palermo Cathedral, this trip is the perfect way to explore the region's diverse culture.
This incredible Italy itinerary packs a lot into five days but doesn't skimp on the luxurious details. Explore Venice to see wide city canals and ornate palaces and feast on fresh seafood, then head to Florence for a private tour of the Accademia Gallery with an art historian and a romantic sunset cruise on the Arno River.