This classic nine-day trip through Italy combines two of its most cultural cities with stops in the beautiful countryside. First, land in Rome to spend quality time in the Vatican and Colosseum before taking a train to Orvieto in the Umbria region—the country's green heart. Spend a night here before you continue to Florence, the birthplace of the Renaissance, where you'll take a walking tour, learn how to make fresh pasta and drive through Tuscany to finish the adventure.


  • Explore Vatican City's museums and Sistine Chapel with a private guide
  • Enjoy free time to see Rome's ancient sights and Centro Storico 
  • Take a sunset walk around Orvieto's medieval walls before dinner
  • Let a local guide show you the best piazzas and cathedrals in Florence
  • Finish a drive through the Tuscan countryside with a wine tasting in Chianti

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome, Explore Rome
Day 2 Self-Guided Visit the Colosseum & Roman Forum Rome
Day 3 Vatican Tour: Museums, Sistine Chapel & St. Peter's Basilica Rome
Day 4 Train to Orvieto, Explore Orvieto
Day 5 Underground Cave Tour & Wine Tasting, Train to Florence Florence
Day 6 Florence Self-Guided City Tour Florence
Day 7 Local Cooking Class in Florence Florence
Day 8 Day Trip to Siena & San Gimignano Florence
Day 9 Depart Florence  

Detailed Itinerary

Day 1: Arrive in Rome, Explore

Take a pinch-me-now walk through Centro Storico to see famous fountains and monuments

Welcome to Rome! According to legend, Italy's capital was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill, which you'll have a chance to see in the coming days. As the longtime center of the mighty Roman Empire, you'll find nearly 3,000 years of architecture, history, and culture throughout the city. After arriving at one of Rome's airports, transfer to your hotel in the historic center. Settle in and then step outside for a stroll. The next few days will involve lots of sightseeing, so spend your first few hours enjoying some of the highlights at a relaxed pace. 

You may want to start at the Catacombs of Priscilla, originally used from the second to fifth centuries as burial grounds for the elite families of Rome. Visitors can see the original structures as well as paintings and artifacts from various periods. Or, simply stroll through the tangle of narrow streets in Centro Storico, one of Rome's most historic districts, to see beautiful fountains and classical Roman and Baroque architecture, including the Pantheon, a 2,000-year-old temple. 

If you have energy left, walk to Colle Aventino, one of Rome's famous seven hills, and Parco Savello (Orange Tree Park), where you can find the renowned keyhole that gives a direct view of the Vatican. This is an excellent place to grab a cappuccino and snack from one of the adjacent cafés. For an authentic market experience, stop by the Mercato dei Fiori, where locals shop for fresh vegetables, flowers, meats, and cheeses. When it's time for dinner, head to the hip Trastevere neighborhood for some of the city's best trattorias.

Day 2: Self-Guided Visit the Colosseum & Roman Forum

Spend the afternoon at the Roman Forum and move at your own pace

Dive deep into ancient Rome today with a self-guided visit to the Colosseum and the Roman Forum with an entrance ticket that combines both sites. It's best to start early to beat the crowds, as walking through the Colosseum is like taking a trip back in time to the days of the Roman Empire. Learn about its illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. Keep an eye out for the Arch of Constantine, which was constructed to honor Emperor Constantine's victory in the battle of Milvian Bridge in 312 CE. 

A short walk from here is the Roman Forum, where you'll see excavations dating back 2,000 years that reveal the ruins of temples, squares, religious sites, and other buildings. These were the venues for public speeches, processions, elections, and gladiator matches. Historians and archaeologists refer to the Roman Forum as the most prominent place in world history, and you'll see why as you admire its grounds. 

Complete your self-guided tour of ancient Rome at Palatine Hill, located 131 feet (40 m) above the city. Take in the incredible views of the city, with the Forum on one side, Circus Maximus on the other, and the Vatican in the distance. After all this exploring, venture to the nearby Monti neighborhood, less than a 10-minute walk, and tuck into a well-deserved meal.

Day 3: Vatican Tour: Museums, Sistine Chapel & St. Peter's Basilica

A private guide will show you some of the Vatican's 54 museums

After an early breakfast at your hotel, you can visit Vatican City's museums and other top sights during a three-hour guided morning tour. The Vatican is rich in history and art, housing some of the most important Renaissance masterpieces in the world. During the tour, you'll visit the Pio Clementio Museum, the Gallery of the Candelabra, the Gallery of Tapestries, and the Gallery of the Geographical Maps

Continue through the museums to the Raphael Rooms, where you can admire the frescoes before entering the incredible Sistine Chapel and St. Peter's Basilica. Your guide will help you experience the allure of Renaissance art by divulging personal details and untold stories throughout the tour.

The rest of the day is free for you to explore on your own. Stroll through more of Rome's historical center to see iconic monuments and architecture, such as the Spanish Steps and Trevi Fountain. Then head over to Piazza Navona and admire the Fountain of the Four Rivers, designed by the iconic Italian sculptor Bernini. Finish your evening with a stroll through the piazza, stopping for pizza, gelato, and people-watching.

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Day 4: Train to Orvieto, Explore

Walk the perimeter of Orvieto for stunning views of the Umbrian countryside

Spend your last few hours taking advantage of any last activities in Rome before you venture north to Orvieto. This medieval hill town is located in the lesser-explored Umbria region of central Italy, which is easily accessible from both Rome and Florence by frequent trains. The small city is home to a stunning cathedral as well as a network of underground caves built by the Etruscans. 

Upon arrival, make your way to your hotel and take the afternoon to explore the historic center on your own or on a guided tour. If you opt for self-guided exploration, you can climb the Torre del Moro for spectacular views from the hilltop town and the surrounding region. Or, head over to the Pozzo di San Patrizio, a historic well town highlights engineering feat is a marvel designed to obtain water from the bluff's depths.

In the early evening, venture to the edge of town and walk along the city walls to take in your beautiful surroundings in this enchanting place. Then head to the center of the city, where the piazzas come to life with bars and restaurants filled with locals. One notable location is the Piazza della Repubblica, where you can enjoy the atmosphere and settle in for a delicious dinner. 

Day 5: Underground Cave Tour & Wine Tasting, Train to Florence

A guide will show you hundreds of human-made caves in Orvieto on this unique tour

Before heading to Florence, take some time in the morning to discover more of what Orvieto has to offer. Meet your guide for a tour of the extensive Underground of Orvieto, made up of more than 400 human-made caves used for an array of purposes across the span of Etruscan history. Travel back in time as you hear stories from your guide before he or she takes you to a locally adored spot nearby for a light lunch and wine tasting. Enjoy sampling local products with a lovely view of the cathedral before saying goodbye to this beautiful city. 

At the appointed time, make your way to the train station to catch an afternoon train to Florence. Once arrived at the station, you'll head to your hotel and freshen up. Start your evening by heading to La Terrazza Continentale next to the Ponte Vecchio for a predinner cocktail on the terrace while you enjoy the sunset. Then make your way to the Sant'Ambrogio neighborhood for dinner accompanied by a glass of Tuscan wine.

Day 6: Florence Self-Guided City Tour

Florence's compact historic center is easy to explore on foot 

Today's exploration of Florence begins with a half-day walking tour. First, meet your guide and then stroll through the picturesque historic center, where you'll find the most important squares and monuments, from the Piazza della Repubblica to the Palazzo Vecchio. You'll then stop at the iconic Duomo and visit Giotto's Bell Tower and the Baptistery, with its bronze doors. Your guide will share stories of the famous Renaissance artists who called Florence home.

After your tour, continue exploring on your own. Consider taking a short walk over to the Mercato Centrale on the second floor of the Mercado di San Lorenzo, where you'll be able to meander through the stalls of local goods. If you're up for an uphill climb, cross over the Arno River to visit Piazzale Michelangelo (or take a taxi). This spectacular viewpoint offers an incredible view of all of Florence. It is the perfect place to watch the sunset before heading to Piazza Santo Spirito for predinner aperitivos

Day 7: Local Cooking Class in Florence

Learn How to Make Traditional Italian Pasta
Learn how to make Tuscan dishes with a local chef during this fun class

Enjoy a leisurely morning in Florence with breakfast at your hotel and a slow stroll through the historic center. Popular highlights that you may not have seen yet include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, with its impressive collections of ancient sculptures and paintings. Be sure to purchase your tickets to the Uffizi online to avoid disappointment!

In the afternoon, you'll meet your host near the center of Florence for a traditional Italian cooking class. He or she will first welcome you with a glass of prosecco as you begin the three-hour experience with an appetizer of Italian cheeses and other local products.

Then roll up your sleeves and learn to cook four Tuscan Italian dishes from recipes passed down through generations. Observe the chef's different tricks and techniques in cooking Italian family recipes. In the summer months, you might be able to use the small vegetable and herb garden in the courtyard where zucchini, tomatoes, and herbs are grown. No matter what the season is, the best part comes at the end when you and your hosts will sit down and enjoy your freshly-made dinner together.

Day 8: Day Trip to Siena & San Gimignano

You'll have free time to wander around the charming streets of San Gimignano 

In the morning, you'll head to the countryside to explore Tuscany on a day trip. Your first stop will be the medieval village of San Gimignano, a UNESCO World Heritage Site located an hour from Florence. Explore the city's beautiful squares, palaces, and churches before taking a break with a coffee in a terraced café. 

In the afternoon, you'll visit nearby Siena, a medieval city with historic sites. You can't miss the great main square, Piazza del Campo, surrounded by the Gothic Pubblico Palace, the Tower of Mangia, and the Gaia Fountain. From here, walk over to the 13th-century cathedral, Duomo di Siena, which dominates the city's skyline. In the summer, the town comes alive with festivities, as the Palio takes place in July and August. This exciting horserace, held twice a year in the main square of Siena, ignites the town in fervor. 

Finish the day with a visit to the medieval fortress town of Monteriggioni, perched on a hillside, where you can explore the intact castle walls. Continue to the Chianti Classico wine region to visit a typical Tuscan winery (with tastings!) before returning to Florence for the evening.

Day 9: Depart Florence

Take a peaceful morning walk around Florence before departure

Say goodbye, or ciao, to Italy for now! Perhaps take a morning stroll to see Florence in a more peaceful light. After breakfast at your hotel—and one more cappuccino—transfer to the airport for your connecting flight home. Safe travels!

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Map of Rome, Orvieto & Florence - 9 Days
Map of Rome, Orvieto & Florence - 9 Days