Itinerary #1: Explore Rome
On this five-day itinerary, you'll uncover layers of history and culture in the Eternal City. Some travelers pass through for a day or two on their way to other destinations, but five days is an ideal amount of time to get a feel for the Roman lifestyle and to visit the Colosseum, the Sistine Chapel, Villa Borghese, and Piazza Navona at a more leisurely pace.
|Day 1||Arrive in Rome||Rome|
|Day 2||Guided Tour of the Colosseum & Bike Tour in the City Center||Rome|
|Day 3||The Vatican Museum, Sistine Chapel & Boat Tour on the Tiber River||Rome|
|Day 4||Art & Food in Rome||Rome|
|Day 5||Depart Rome|
This five-day trip plan begins in the historic center of Rome and one of the city's oldest sites: the Catacombs of Priscilla, dating from the second century, originally dug as burial grounds for the city's aristocratic families. Afterward, stroll past the Colonna di Marco Aurelio landmark on your way to Colle Aventino, one of Rome's seven hills known for its rose gardens and cafés. Wander through the Mercato dei Fiori market to see Romans doing their daily shopping. On Day 2, enjoy a guided tour of gladiator history at the Colosseum, followed by a three-hour bicycle tour past Piazza Navona, Trevi Fountain, and the Pantheon.
You'll spend your third day at the Vatican Museum, visiting the Sistine Chapel and St. Peter's Basilica. Then, board a boat to view the city from the Tiber River, passing beneath Rome's most famous bridges, including Saint'Angel Bridge, Sisto Bridge, and Garibaldi Bridge. Day 4 is devoted to the pleasures of art and food: see the works of Bernini, Caravaggio, Canova, and Rafaello at the elegant Galleria Borghese. Take some time for a stroll around the gardens of Villa Borghese before heading to a cooking class where you'll learn how to make a traditional pizza. On Day 5, wrap up the trip with a classic Roman colazione (breakfast) of espresso and pastries. Learn more
And check out this article for ideas on how to get off the beaten path in Rome.
Itinerary #2: Naples & the Amalfi Coast
Ideally, you'd have weeks to sightsee in Naples and linger on the Amalfi Coast. But this five-day itinerary is enough to enjoy some of the region's highlights, from the ruins of Pompeii to seafood on the beach. And—of course—a pizza napolitana (Naples-style pizza) or two.
|Day 1||Arrive in Naples||Naples|
|Day 2||Pompeii and Mount Vesuvius||Naples|
|Day 3||Explore Naples, Transfer to Maiori||Maiori|
|Day 4||Visit Amalfi & Positano||Maiori|
|Day 5||Depart Naples|
The adventure begins in Naples. Spend the morning at the Naples Archaeological Museum viewing artifacts from nearby Mount Vesuvius, or stop into the 16th-century Museo Cappella Sansevero to view an impressive sculpture collection. Then head to the seaside castle of Castel dell'Ovo or take a short excursion out of the city to see Solfatara, a dormant volcano located a half-hour drive west of Naples. In the evening, walk along the waterfront promenade of Caracciolo e Lungomare di Napoli before sitting down for dinner at a family-run trattoria in the Quartieri Spagnoli.
On Day 2, you'll tour the ruins of Pompeii (buried in ash during the eruption of Mount Vesuvius in 79 CE) before heading to the volcano itself. The following day, spend time sightseeing in Naples before taking an afternoon side trip to the coastal village of Maiori. A laid-back walking tour takes you to the town's main attractions, including Castello di San Nicola, a 15th-century fortress, terraced gardens and sea views at the Giardino Esotico Beniamino Cimini, and Santa Maria de Olearia, a historic abbey built into the cliffside.
On Day 4, explore the white-washed houses and churches of Amalfi. Have a coffee with a view of the Duomo on La Piazzetta di Sant'Andrea, the city's main square. Have a snack, too: next on the agenda, you'll be walking three hours to the charming village of Ravello before moving onto colorful Positano. From town, you can take off on Amalfi's most famous hiking trail, the Path of the Gods. Finally, end the trip back in Naples: a walk along Via Toledo, the main shopping street, is a perfect place to pick up some souvenirs. Learn more
Itinerary #3: Explore Western Sicily
Sicily is larger than many travelers imagine. If you have just five days, it's best to concentrate your energy and time on one region. This itinerary, focused on western Sicily, takes you to ancient temples, lively street markets, and beautiful beaches.
|Day 1||Arrive in Palermo||Palermo|
|Day 2||Guided Tour of Palermo||Palermo|
|Day 3||Full day in Cefalù||Palermo|
|Day 4||Day Trip to Segesta & Erice from Palermo||Palermo|
Begin your trip in the old city of Palermo, located on the shores of the Gulf of Palermo. Tour the historic center, stopping in the 12th-century Monreale Cathedral, the Galleria Regionale, a 16th-century neo-Gothic castle, and the Convento dei Cappuccini's Catacombs, home to thousands of mummies. At night, go for fresh seafood and a glass of local wine in one of the city's many quaint family-run restaurants. On Day 2, a guided tour takes you to the largest house in Italy, Teatro Massimo, and Fontana Pretoria, a 16th-century fountain. Afterward, stroll along the harbor promenade and wander the lovely gardens at I Giardini Inglese and Villa Garibaldi.
On Day 3, catch the train for a quick ride to the seaside resort of Cefalù. Stroll the promenade or the lungomare, a popular sandy beach, before visiting the 17th-century Bastione di Capo Marchiafava. The following day, head to Segesta, an archaeological complex known for its 2,400-year-old Greek temple that stands alone on a pedestal hill. After a walking tour of the site, detour to the medieval city of Erice, famous for its narrow streets, medieval arches, and charming courtyards. Climb the bell tower of the 14th-century Duomo for a view of the city. Finish the trip back in Palermo, lingering over a cappuccino at a sidewalk café. Learn more
Find out when's the best time to visit Sicily here.
Itinerary #4: Cycling Tuscany: Florence to Siena
Eager to see Tuscany on two wheels? This five-day itinerary is the one for you. Bicycles are a great way to get around the city of Florence—and a great option for covering the ground between classic Tuscan destinations, passing grand castles, and rolling vineyards along the way.
|Day 1||Arrive in Florence||Florence|
|Day 2||Florence to Radda-in-Chianti||Radda-in-Chianti|
|Day 3||Radda-in-Chianti to Siena||Siena|
|Day 4||Siena to Montalcino Loop||Siena|
|Day 5||Depart Siena|
Squeeze in some sightseeing in Florence on the first day of your trip. Visit the Duomo, sit in a sunny plaza for lunch, and linger on Ponte Vecchio bridge at sunset. On Day 2, you'll have an early start, heading off on a bicycle toward Impruneta, known for its famous basilica, the Sanctuary of Santa Maria, and Mercatele, a small town in the heart of Chianti country. Pedal along the Tuscan wine road, stopping for a glass of wine in Greve's pretty square. You'll spend the night at the medieval Pretorio Palace before continuing on Day 3 toward Castagnoli. Stop at the Castle of Brolio for a quick wine tasting. By evening, you'll reach Siena.
Siena's historic center is a UNESCO World Heritage Site. Enjoy exploring it on the morning of Day 4: highlights include the Gothic Siena Cathedral and Piazza del Campo, home of the Palio, Siena's famous biannual horse race. Today you'll embark on a loop around Tuscan wineries and villages, including the renowned Brunello vineyards, a wine tasting at Montalcino, the walled city of Asciano, and the nearby Monte Oliveto Abbey. Ride back to the city on roads that cut through olive groves and vineyards. Savor your last evening (and the following morning) in Siena. Learn more
Learn more about your options in the region with this guide to getting off the beaten path around Florence.
Itinerary #5: Tour Northern Italy from Milan
In five days, you can do a lot in northern Italy. This busy itinerary takes travelers to Milan, Lake Como, Bologna, and Turin, with plenty of time to enjoy the region's art, aperitivo culture, and views of the snow-capped Alps.
|Day 1||Arrive in Milan||Milan|
|Day 2||Lake Como||Milan|
|Day 3||Discover Bologna||Milan|
|Day 4||Explore Torino||Milan|
|Day 5||Depart Milan|
Start in Milan, touring the city's historic sites, including the Cathedral—the largest church in Italy and the 16th-century Royal Palace. Stop for a coffee or a glass of wine at the pedestrianized Galleria Vittorio Emanuele II. Later in the day, explore the city's ancient network of canals at the Navigli at Porta Genova. It's the perfect place to join in the city's aperitivo scene: think happy hour, Italian-style. On Day 2, you'll tour the 14th-century cathedral and the Museum of Silk in Lake Como to learn about the region's historic silk industry, then catch a ride on the funicular railway to take in views from high above.
Later, take a quick boat ride to Bellagio before returning to Milan for dinner and drinks. The following day, head to Bologna to walk the historic city: highlights include the Piazza Maggiore, the large central plaza, the 14th-century Basilica di San Petronio, the Jewish Ghetto, and the National Art Gallery. Try a local specialty like tortellini with ragu alla bolognese for lunch. On the last full day, train Turin, the capital of the Piedmont region. After a guided walking tour, in the morning, you'll visit the Parco Archeologico Torri Palatine to see the Palatine Towers, Roman city walls that date back to the first century, in the afternoon. Head back to Milan for a northern Italian feast and at least one more spritz in the company of locals. Learn more
For more on Italy's best lakes, check out this ultimate guide.
More Great 5-Day Italy Itineraries
Looking for more inspiration for your Italy trip? Check out these other five-day Italy itineraries, with outdoor adventures, cultural trips, and best-of tours to hit the highlights.