Italy 5-Day Tours & Itineraries

Explore 28 trips designed by local kimkim specialists to get ideas for your trip to Italy.

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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View of the Amalfi Coast
Map of Naples & Amalfi Coast - 5 Days
Naples & Amalfi Coast - 5 Days

This packed five-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 Mount Vesuvius, and visit the colorful bohemian Positano on the Amalfi Coast. Make sure you try the Naples pizza—the Amalfi Coast's real highlight. 

Bellagio reflected in Lake Como in northern Italy
Map of Explore Northern Italy from Milan - 5 Days
Explore Northern Italy from Milan - 5 Days

Explore Northern Italy's cities and landscapes in this packed five-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 the 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 cafés and aperitivo bars.

Polignano a Mare, Puglia
Map of Best of Puglia: Lecce, Otranto, & Alberobello - 5 days
Best of Puglia: Lecce, Otranto, & Alberobello - 5 days

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.

Colorful Cinque Terre
Nature in Italy: Lake Como and Cinque Terre - 5 Days

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.

Florence's City Skyline and the Ponte Vecchio Bridge
Map of Explore Tuscany: Florence, Siena, Pisa & More - 5 Days
Explore Tuscany: Florence, Siena, Pisa & More - 5 Days

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.

Take in the setting sun over Palmero
Map of Palermo and Surroundings - 5 Days
Palermo and Surroundings - 5 Days

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.

Bellagio, Lake Como
Map of Exploring The Villages of Lake Como - 5 Days
Exploring The Villages of Lake Como - 5 Days

Explore three beautiful villages of Lake Como on a quick 5-day trip to Northern Italy. Learn about the history of Como during a guided tour of  Villa Olmo and the Basilica of San Fedele. Take a scenic ferry ride to travel to the traditional village of Varenna. Learn about the significance of iconic villas including Villa Monastero in Varenna, then hop across to Bellagio by boat to visit the botanical gardens of Villa Serbelloni and the neoclassical Villa Melzi.

Galleria Vittorio Emanuele II shopping mall
Map of The Best of Milan & Lake Como - 5 Days
The Best of Milan & Lake Como - 5 Days

Explore the best of Northern Italy on this 5-day trip to Milan and Lake Como. Milan is a city full of Rennaissance art and historic architecture, as you'll experience as you visit its famous Gothic Duomo and other highlights. Learn how to make fresh pasta and Italian cocktails during a cooking class, and take a day trip to Lake Como and visit the beautiful villages of Bellagio, Varenna, and Como.

View of the Amalfi Coast
Map of Rome & the Amalfi Coast - 5 Days
Rome & the Amalfi Coast - 5 Days

This 5-day adventure fits it all in, from the highlights of Rome to the sunny beaches of the Amalfi Coast. Start your trip exploring the historical sites and monuments of the Eternal City before heading down south to discover the ruins of Pompeii and Mt. Vesuvius. Finish things off with the blue waters of Capri and the dramatic landscapes of the Amalfi Coast.

Skyline of Rome
Map of Explore Rome - 5 Days
Explore Rome - 5 Days

Discover historical and modern highlights of the Eternal City in this five-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.

Get various viewpoints of Florence's iconic skyline on this itinerary
Map of Highlights of Florence - 5 Days
Highlights of Florence - 5 Days

You don't need more than five days to have a fantastic trip to Florence. This itinerary covers a great deal of ground, including Renaissance masterpieces, bustling food markets, and elegant gardens. You'll even take a pasta-making class and spend a day in Tuscany visiting gorgeous hill towns, a Chianti winery, and a medieval city—Siena—known for a world-famous horse race.

Erice cityscape
Map of Explore Western Sicily - 5 Days
Explore Western Sicily - 5 Days

Explore western Sicily on this five-day trip, from cultural Palermo to sunny Cefalù. You'll see medieval churches, tour the macabre Caphucin Catacombs, and soak in the sunshine on Cefalù'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. 

Skyline of Rome
Highlights of Rome and Florence - 5 Days

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.

Ancient Roman Forum in Rome
Map of Luxury Italian Highlights: Venice & Florence - 5 Days
Luxury Italian Highlights: Venice & Florence - 5 Days

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.

Bicycles are a great way to get around Florence and the surrounding region
Map of Cycling Tuscany: Florence to Siena - 5 Days
Cycling Tuscany: Florence to Siena - 5 Days

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.

Piedmont Countryside
Map of Food & Wine in Piedmont: Turin, Alba & Barolo - 5 Days
Food & Wine in Piedmont: Turin, Alba & Barolo - 5 Days

Enjoy some of Italy's finest food and wine with this 5-day trip to the Piedmont region. Explore Turin's city center and learn about its food scene from a local guide on a street food tour. Try local specialties including bicerin and grissini. Discover the medieval town of Alba and the surrounding Langhe Hills wine region with a full-day tour to several small wineries and villages where Barolo and Barbaresco wines are produced.

Scaliger Castle in Sirmione
Luxury Italian & Swiss Lakes by Train - 5 Days

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.

St. Mark's Square, Venice
Map of Highlights of Venice, Verona & Lake Garda - 5 Days
Highlights of Venice, Verona & Lake Garda - 5 Days

With this quick 5-day trip, you'll explore Venice and the Veneto region of Northern Italy. Experience the heart of the 'Floating City' as you wander along its beautiful canals and visit St. Mark's Square and the Palazzo Ducale (Doge's Palace). Experience Shakespearean love in Verona at Casa di Giulietta and relive Roman entertainment at the Arena. Take a day trip to Lake Garda and find tranquility in the picturesque lakeside villages of Sirmione and Desenzano del Garda.

Lake Garda views
Map of Explore Scenic Lake Garda - 5 Days
Explore Scenic Lake Garda - 5 Days

Explore the best of Lake Garda with this quick 5-day itinerary. Experience the relaxed pace of life at the southern end of the lake and visit Roman villas and medieval castles on a guided tour of Sirmione and Peschiera del Garda. To the north is Riva del Garda, a town influenced by Austrian and Italian culture. Enjoy outdoor activities and take a self-guided day trip to the picturesque village of Malcesine.

Portofino coastline
Luxury Northwest Italy: Turin, Cinque Terre, Riviera - 5 Days

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.

Wine tasting in Chianti
Exploring Italian Wines in Tuscany and Cinque Terre - 5 Days

Embark on a five-day Tuscan tour, savoring the region's delicious fresh produce and fine wines, strolling medieval piazzas in hilltop towns like Siena, Volterra, and San Gimignano, and concluding with a visit to dazzling Cinque Terre for aperitivo and Ligurian cuisine with unbeatable sea views.

Francigena Way, Tuscany, Italy
Map of Via Francigena: San Miniato, San Gimignano, & Siena - 5 Days
Via Francigena: San Miniato, San Gimignano, & Siena - 5 Days

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.

Homemade bread and olives
Map of Food & Wine in Bologna & Milan - 5 Days
Food & Wine in Bologna & Milan - 5 Days

Take a trip through the food and wine region of Emilia-Romagna with this 5-day itinerary. Delve deep into Bologna's historic city center, visiting the iconic university and the Quadrilatero district. Spend a day in Parma to learn about the production processes of prosciutto and Parmigiano Reggiano and, of course, taste the final products. Learn from an Italian chef in Milan as you prepare fresh pasta and mix cocktails at a guided cooking class.

Tuscany, Italy countryside
Map of Tuscany By Bike: San Gimignano, Montalcino, Siena - 5 Days
Tuscany By Bike: San Gimignano, Montalcino, Siena - 5 Days

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.

Colorful Houses, Italian Riviera
Map of Grand Cities and Classic Riviera Villages: Turin, Santa Margherita Ligure, Cinque Terre, & More - 5 Days
Grand Cities and Classic Riviera Villages: Turin, Santa Margherita Ligure, Cinque Terre, & More - 5 Days

With 5 days to spend,  discover Turin and the Italian Riviera in Northern Italy. Explore Turin's historical city center with a guide and visit grand piazzas, palaces and museums. After, journey to Santa Margherita Ligure on the Italian Riviera, the perfect picturesque beachfront village. Spend time relaxing in beautiful Portofino and enjoy a day trip to the Cinque Terre, famous for its medieval villages, dramatic sea cliffs, and world-class hiking trails.

Gondola Ride, Venice
Map of Discover Treviso, Venice and Verona - 5 Days
Discover Treviso, Venice and Verona - 5 Days

Enjoy a fast 5-day trip to Treviso and Verona, two cities with rich and interesting histories. Discovering ornate churches, interesting museums, and vintage clothing boutiques in Treviso. Travel back in time in Verona on a guided tour of ancient castles and grand piazzas. Spend a day in Venice, walking through the former Jewish Ghetto, the Rialto market towards Piazza San Marco at the center.

Isola Bella, Lake Maggiore
Map of Historic Milan & Romantic Lake Como - 5 Days
Historic Milan & Romantic Lake Como - 5 Days

With this quick 5-day trip, discover Milan and the grandeur of Lake Como. Experience elegant villas, charming cobblestone lanes, and romantic gardens in Bellagio, explore the historic center of the town of Como, and take in the views from a funicular at sunset. Delve into centuries of Italian history at Milan's Duomo, admire Da Vinci's masterpiece "The Last Supper", and get a feel for local life in the capital of Italian culture.

Italian food and wine
Map of Food & Wine in Verona & Padua - 5 Days
Food & Wine in Verona & Padua - 5 Days

In 5 days, you'll enjoy great food and wine tours, sampling Italian cuisine, regional specialties and local wines. You'll also take a crack at crafting handmade pasta during a cooking class in Verona. Visit a rural olive farm and Veneto wineries close to Padua, and explore that city's medieval center, the artistic masterpieces of Giotto, and Europe's first botanical garden.

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