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||Arrival in Rome||Rome|
|Day 2||Guided Tour of the Colosseum and Bike Tour in the City Center||Rome|
|Day 3||The Vatican Museum, Sistine Chapel, and 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 2nd 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 two, 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 four 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 Roman cooking class where you'll learn how to make a traditional pizza. On day five, 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: Discover 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||Welcome to 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 two, 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. Now a UNESCO Biosphere World Reserve, Mount Vesuvius is laced with hiking trails. The following day, take some time for sightseeing in Naples before taking an afternoon side trip to the coastal village of Maiori. A laid-back walking tour takes you 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 four, 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: Adventure in 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||Arrival 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|
|Day 5||Goodbye Italy!|
Begin your trip in the old city of Palermo, located on the shores of the Gulf of Palermo in the Tyrrhenian Sea. Tour the historic center, stopping in the 12th-century Monreale Cathedral, the Galleria Regionale, a neo-Gothic castle that dates from the 15th century, 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 two, a guided tour takes you to the largest house in Italy, Teatro Massimo, and Fontana Pretoria, a 16th-century fountain. Stroll along the harbor promenade afterward and wander the lovely gardens at I Giardini Inglese and Villa Garibaldi.
On day three, catch the train for a one-hour ride to the seaside resort of Cefalù. Catch a breeze on the seaside promenade or on the lungomare, a popular sandy beach, before visiting the 17th-century Bastione di Capo Marchiafava, a defensive fortress offering sweeping views over the coastline. The following day, day-trip to Segesta, an archaeological complex known for its 2400-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: Cycle through 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 two, 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 the pretty square in the town of Greve. You'll spend the night at the medieval Pretorio Palace before continuing on day three toward Castagnolli. 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 four: 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|
There's so much to see and do (and eat and drink) in northern Italy. Start in Milan, touring the city's historic sites, including the Cathedral—the largest church in Italy and the fourth-largest in the world—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 two, day-trip to Lake Como. You'll tour the 14th-century cathedral and the Museo Didattico della Seta (Museum of Silk) 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 the town of Bellagio for a relaxed cappuccino or a late lunch at a lakefront restaurant. Head back to Milan for dinner and drinks. You'll need some rest before the next day's side trip to Bologna, a two-hour journey by train. Tour the historic city on foot: highlights include the Piazza Maggiore, the large central plaza, the 14th-century Basilica di San Petronio, the Jewish Ghetto, and the Pinacoteca Nazionale di Bologna (the National Art Gallery). Try a local specialty like tortellini with ragu alla bolognese for lunch before wandering through the city's covered walkways, which conveniently connect city landmarks.
On the last full day of the trip, take a one-hour train ride from Milan to Torino (Turin), capital of the Piedmont region. After a guided walking tour in the morning, including stops in the 16th-century Palazzo Reale (the Torino Royal Palace) and the baroque Chiesa di San Filippo Neri, Torino's largest church, have a glass of Barolo on one of the city's many piazze (squares). In the afternoon, visit the National Cinema Museum, housed in a 19th-century Jewish synagogue, or the Parco Archeologico Torri Palatine to see the Palatine Towers, Roman city walls that date back to the 1st century. 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 Unique Itineraries in Italy
More Great 5-Day Italy Itineraries
Looking for more inspiration for your Italy trip? Check out these other 5-day Italy itineraries, ranging from active, to cultural, to luxury, or family-friendly trips.
Or, describe your ideal trip and we will connect you with a local specialist to make it happen.