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
Five days is enough time to enjoy any number of activities in any region of Italy. If culture and history are your interests, then you can explore the ancient streets of Rome. If you want more of an active adventure, cycling through the famous wine-producing region of Tuscany is an option. You could even make an excursion from the fashion-and-nightlife haven of Milan to the gorgeous lakes and snow-capped Alps of Italy’s far north.
See our itineraries below or read our guide to the best 5-day trips in Italy.
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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.
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.
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.
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.
Enjoy northwestern Sicily's top city with this 5-day tour of Palermo and its surroundings. Go on a street food tour of the regional capital after admiring the city's intricate baroque architecture before making a day trip to the stunning Doric temple of Segesta. End your quick trip with a day spent in the popular seaside town of Cefalù where you'll climb the Rocca for striking views, swim in the inviting Tyrrhenian Sea, and sip an afternoon apertivo while taking in the setting sun.
Explore Northern Italy's natural charm starting with Lake Como, where you'll take a boat tour of its extravagant shore lined with mansions. Ride the funicular to the scenic vista in Brunate where you'll catch a panoramic view of Como and the stunning surrounding nature. Transfer to colorful Cinque Terre, where you'll hike from one seaside village to another while enjoying breathtaking sunsets and views of the Ligurian Sea.
Explore Puglia, the "heel of Italy," one of the country's southernmost regions, which welcomes visitors with olive trees, a sparkling turquoise sea, and whimsical towns and villages. Take a walking tour through Lecce, snap photos of the iconic trulli homes in Alberobello, and enjoy the beaches and cuisine this region is famous for.
Take a five-day frolic through Italy and Switzerland with this itinerary. You'll split your time between lakes and mountains, often enjoying views of both simultaneously, as you take in waterfront historic sites, luxurious villas, and more.
Tuscany is famous for its beautiful landscapes, vineyards, cypress trees, farms, and medieval hill towns. What better way to experience some of the best views in Italy than by bike. You'll explore the hills and towers of San Gimignano, have a chance to taste Brunello wines in Montalcino, and learn about the history and architecture of Siena.
Catch a glimpse of luxuries of Northwest Italy with this five-day itinerary. You'll spin through seaside towns of Portofino and Cinque Terre, then go inland to hunt for truffles in the Langhe region. End in the city of Turin with an insider tour of its most historic spots.
In 990 BCE, the Archbishop of Canterbury traveled from England to Rome to meet with the Pope. He wrote a detailed diary of the 80 stages of his journey through the United Kingdom, France, and Italy, and this path is now known at the Via Francigena (the Francigena Way), a path for religious pilgrims from Canterbury to Rome. The trail travels through Tuscany, and you can experience it on this five-day itinerary that winds through the Tuscan countryside.
Indulge your taste buds on this Tuscan tour, visiting beautiful vineyards and medieval towns like Siena, Volterra, and San Gimignano, where you'll enjoy the flavors of the region with wine tastings and traditional, locally-sourced cuisine. Explore ancient cobblestone streets and monuments, enjoy the old Cypress trees of Bolgheri, and sleep soundly in your cozy farmhouse accommodation. End your trip on the rocky coast of Cinque Terre where you'll enjoy more wine and regional foods, plus one last stop at the Leaning Tower of Pisa.
Start your 5-day trip by discovering the sites of Rome with a guided tour through historic cathedrals, squares, museums, and bridges, plus enjoy incredible views atop one of its seven hills. Visit Vatican City, perusing its Renaissance art through museums, the Sistine Chapel, and St. Peter's Basilica, then head to Florence to discover its famous Duomo and the statue of David in the Galleria dell'Accademia. Finish the tour with a visit to Lucca and Pisa, two Tuscan cities with history that goes beyond the Leaning Tower.