This route takes you through the highlights of Italy while exploring more of each region. Start in Rome, visiting the Vatican and Colosseum before making your way up to the lesser-known Umbria region for a stopover in Orvieto. Enjoy your time away from the big city and delight in the local life. Continue up to the birthplace of the Renaissance, Florence. This city's incredible plazas and cathedrals never disappoint.


  • Explore the world-famous Vatican Museum and Sistine Chapel
  • Discover ancient legends and Rome's darker side at the Colosseum
  • Explore the lesser-known and stunning Umbria region of Italy
  • Tour Florence's beautiful medieval piazzas & cathedrals
  • Enjoy a full day in medieval towns in Tuscany

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome Rome
Day 2 Vatican Tour: Museums, Sistine Chapel & St Peter’s Basilica Rome
Day 3 Self-Guided Tour of Historic Rome Rome
Day 4 From Rome to Orvieto Orvieto
Day 5 Underground Tour & Wine Tasting in Orvieto Orvieto
Day 6 From Orvieto to Florence Florence
Day 7 Florence Self-Guided City Tour Florence
Day 8 Local Cooking Class in Florence Florence
Day 9 Tuscany Day Trip: Siena & San Gimignano Florence
Day 10 Goodbye Italy  

Detailed Itinerary

Day 1: Arrive in Rome

Streets of Trastevere, Rome
Streets of Trastevere, Rome

Welcome to Rome, known as the City of the Seven Hills! According to legend, Rome was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill. As the long-time center of the powerful 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, you'll transfer to your hotel in the historic center. Settle in and relax, then head out for a stroll and your first look at the Eternal City. The next few days will involve lots of sightseeing, so spend your first few hours enjoying some of the highlights. Suggested activities include:

  • Visit the Catacombs of Priscilla, which were originally used from the 2nd to 5th centuries as burial grounds for the elite families of Rome. After the entrance was blocked for centuries to protect against grave robbers, the catacombs were rediscovered in the 16th century. Visitors can see the original structures as well as paintings and artifacts from various time periods. 

  • Stroll through the tangle of narrow streets in Centro Storico, one of Rome's most historic districts, to see classical Roman and baroque architecture. 

  • Stop to see the Colonna di Marco Aurelio, a Doric column with a spiral of relief sculptures. It was erected in the 2nd century C.E. to celebrate the victories of the emperor Marcus Aurelius. 

  • Head to the Colle Aventino, one of Rome's famous seven hills. Stroll through the Roseto Comunale, the rose garden which sits on the site of a former Jewish cemetery. Then continue to Parco Savello (Orange Tree Park), where you can find the famous keyhole that gives visitors a direct view of the Vatican. Grab a cappuccino and snack from one of the adjacent cafes.

  • For an authentic market experience, stop by the Mercato dei Fiori, where locals shop for fresh vegetables, flowers, meats, and cheeses. Browse for authentic Italian pasta and other souvenirs, then take a break with coffee and a pastry at one of the many cafes surrounding the market. 

For dinner, head to the Trastevere neighborhood for some of the city's best trattorias.

Day 2: Vatican Tour: Museums, Sistine Chapel & St Peter’s Basilica

St. Peter's Square and the Vatican

Today you will visit the Vatican City museums and Sistine Chapel, as well as other top sights in a 3-hour guided tour of the city's incredible art and history. The Vatican is not only rich in history, but also in art, housing some of the most important Renaissance masterpieces in the world. You'll visit the Pio Clementio Museum, plus 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 secret details and untold stories throughout the tour.

The rest of the day is free for you to explore on your own. Stroll through the Centro Storico, the historic center, of Rome wander past iconic monuments and architecture such as the Spanish Steps and Trevi Fountain. 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 some pizza, gelato, and people-watching.

Day 3: Self-Guided Tour of Historic Rome

Visit the Colosseum
Visit the Colosseum

Lose yourself in the Eternal City on a full-day self-guided walking tour. All told, this route covers four miles (6.5 km), but we'd recommend starting early and giving yourself the entire day to get the most out of the landmarks- especially if you're planning on visiting the inside of the Colosseum and Roman Forum.

Recommended Schedule

Your starting point is Termini Station, the main railway terminal in Rome. From here it's a short walk to the Colosseum, one of the New 7 Wonders of the World. It was built in 80 CE with a capacity for 80,000 guests, which also made it the largest arena for its time. And just northwest of the Colosseum is the Roman Forum. This historic area was the heart of ancient Rome and dates to around the 7th century BCE. Inside, you'll explore numerous ruins of government buildings and temples from the time of the Roman Republic and the Roman Empire. If you're planning to explore the interiors of either of these sites, purchase your tickets online ahead of time to avoid long lines, and give yourself the full morning (around 4 hours) to properly visit. 

After your visit, it's the perfect time to take advantage of your surroundings and Rome's cuisine. Venture to the nearby Monti neighborhood- less than a 10-minute walk- to tuck into a well-deserved lunch. 

After lunch, continue on to Piazza Venezia, located at the end of the Roman Forum. It's home to the Victor Emmanuel II Monument, which was built in the 19th century to honor the first king of unified Italy. To locals, it's known simply as the "wedding cake" due to its white-washed exterior and wide, colonnaded portico. 

You'll also stop at Campo de' Fiori. This plaza is home to Rome's oldest outdoor market, the Mercato dei Fiori, which has has been selling fresh produce and flowers since 1869. Then it's off to one of the true icons of the city, the Pantheon, the only pagan temple in Rome left intact. Piazza Navona is another popular stop, as it's home to the Fountain of the Four Rivers. Designed by the legendary Italian sculptor Bernini in 1651, it features four river gods gathered around a towering Egyptian obelisk.

Another highlight is the Castel sant' Angel, a fortress sitting on the banks of the Tiber River. It was originally commissioned in 134 CE as a mausoleum for Emperor Hadrian, and today it's a museum. You'll round out the tour with stops at the stunning Spanish Steps and Trevi Fountain, the most famous staircase and fountain in the city, respectively.

In the evening head to the Trastevere neighborhood for dinner at an osteria or a trattoria, followed by drinks at a trendy wine bar.

Day 4: From Rome to Orvieto

Orvieto Cathedral

Discover the lesser-explored Umbria region of central Italy. Easily connected to both Rome and Florence by frequent trains and almost equidistant between these two larger cities, Orvieto makes for the perfect stop to compliment your travels. With its hilltop location and medieval architecture, the city is home to a stunning Cathedral as well as a network of underground caves built by the Etruscans. 

From Rome, set out by train or self-drive your way the 2 hours into Umbria. Once you arrive in Orvieto, make your way to your hotel. Take the afternoon to explore the historic center on your own or with a guided tour.

If you opt for some self-guided exploration, we suggest climbing the Torre del Moro for some spectacular views from this hilltop town to the surrounding region. Or, head over to the Pozzo di San Patrizio, a historic well and a highlight of the town. This engineering feat is a marvel was designed to obtain water from the depths of the bluff it sits on. From there, venture to the edge of town and walk along the city walls to take in your beautiful surroundings in this enchanting place.

In the evening, head to the center of the city where the piazzas come to life with and bars and restaurants fill up with locals. Head to Piazza della Repubblica to enjoy the atmosphere and settle in for a delicious dinner.

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Day 5: Underground Tour & Wine Tasting in Orvieto

Hilltop town of Orvieto

Spend the day exploring Orvieto and discovering all it has to offer. Around midday, meet your guide to begin your journey back in time on a 2-hour tour of Orvieto's Underground City. Make your way to the entrance of the grottos and underground tunnels hidden inside the cliffside of Orvieto. Created by the inhabitants of the city approximately 2500 years ago, you'll set out to discover the extensive underground of Orvieto. This hour-long route inside the well-lit cave-like labyrinth is easily accessible alongside your local guide.

Journey your way back across thousands of years of history, hearing the stories that this unique geologic wonder has born witness to from your guide.  Orvieto's underground has served many purposes spanning Etruscan history, and these seemingly endless tunnels, passageways, and caverns make up an incredible ancient adventure to discover. What started first as wells and cisterns to hold water expanded over time to include cellars, shelters, and even spaces for the production of goods like pottery. 

After your visit, come back to the present day and continue to see what makes modern Orvieto special. Your guide will take you to a locally beloved spot nearby for a light lunch and wine tasting. With a lovely view of the Duomo to enjoy throughout your lunch, sample an array of local products such as white wine, cured meats, and cheeses. Take the rest of the afternoon to continue to explore Orvieto on your own.

Day 6: From Orvieto to Florence

Florence skyline

Make your way to the train station to catch an afternoon train from Orvieto into Florence. Once arrived at the station, you'll head to your hotel and settle in.  Afterward, head out on your own for a relaxing stroll and dinner downtown.

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. Make the most of your time at some of these spots:

  • Head to Studio Artemisia, located steps away from the Ponte Vecchio for a class in ancient fresco painting techniques
  • Visit the Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats and cheeses, and a variety of lunch spots
  • Take a walk through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery

We suggest heading to La Terrazza Continentale next to the Ponte Vecchio bridge for a pre-dinner 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 7: Florence Self-Guided City Tour

Piazza della Signoria, a UNESCO site
Piazza della Signoria, a UNESCO site

Spend the day strolling the streets of Florence and exploring this incredible city with this suggested self-guided route. All together, the route is just a couple of miles, but take your time to enjoy the sites along the way for a full-day experience.

Start your day at the iconic Duomo, the earlier the better! Also known as the Cathedral of Santa Maria del Fiore, Florence’s Duomo is the third-largest church in the world. Entrance into the main sanctuary is free - but keep in mind a modest dress code. As there is often a line to get in, give yourself an hour to properly visit this iconic spot. 

From there, make the 5-minute walk over to the Mercato Centrale, on the second floor of the San Lorenzo market, where you'll be able to stroll through the stalls of local goods and grab a morning coffee to start your day.  Give yourself an hour or two to soak in the sights and smells, and to buy some traditional leather goods as souvenirs. After, the nearby Piazza della Republica is the perfect place to soak in the atmosphere of Florence's city center and the incredible architecture that embodies it. 

Take a moment to pass through Piazza della Signoria, where replicas of famous statues, including that of Michelangelo's David, line the square and give it an incomparable air of elegance before stopping for lunch nearby.

Across this same piazza, you'll find the entrance to the Uffizi museum. Even if you decide not to make a stop to peruse the expansive art collection, you can cross through its courtyard, Piazzale degli Uffizi, to make your way to the Ponte Vecchio. This famed bridge is now dotted with jewelry shops and is an iconic sight in the Florence cityscape. Cross the bridge and get a glimpse of the Arno River underneath from its many angles. 

End your day with a visit to Piazzale Michelangelo. It's a bit of an uphill climb or a quick taxi ride away. This spectacular viewpoint offers an incredible sight of all of Florence and is the perfect place to watch the sunset before you head over to Piazza Santo Spirito for some pre-dinner aperitivos. 

Day 8: Local Cooking Class in Florence

Learn How to Make Traditional Italian Pasta
Learn How to Make Traditional Italian Pasta

Enjoy a leisurely morning in Florence, with breakfast at your hotel and a few slow strolls through the historic center. Popular highlights include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, which houses works by artists like Michelangelo and Leonardo de Vinci. 

In the afternoon, you'll meet your host near the center of Florence for a traditional Italian cooking class. They'll welcome you with a glass of prosecco. Enjoy the venue as you begin the experience with an appetizer of Italian cheeses and other local products.

Next you'll roll up your sleeves and learn to cook regional Italian pasta from recipes passed down through generations. Your hands-on Italian cooking class will last about three hours. You'll learn to cook four dishes from scratch, including a side or dessert. Observe the chef's different tricks and techniques involved 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. 

The best part of the class is at the end, where you'll enjoy your freshly-made dinner in a traditional Italian style, shared with your hosts.

Day 9: Tuscany Day Trip: Siena & San Gimignano

Cathedral and Historic Center of Siena
Cathedral and Historic Center of Siena

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

In the afternoon, you'll visit nearby Siena, a medieval city brimming with historic sites. You can't miss the incredible main square, Piazza del Campo, which is surrounded by the Gothic Pubblico Palace, the Tower of Mangia, and the Gaia Fountain. Walk over to the 13th-century cathedral, Duomo di Siena, which dominates the skyline of the city. In summer months, 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 a fervor. 

Finish the day with a visit to the medieval fortress town of Monteriggioni. The intact castle walls surround the town, perched on a hillside, and is a sight to behold. Continue onto the Chianti Classico wine region to visit a typical Tuscan winery before returning to Florence for the evening.

Day 10: Goodbye Italy

Sunset over Florence
Sunset over Florence

Your exploration of Italy will end after breakfast, with a transfer to the airport to catch your flight home or to your next destination.


Map of Rome, Orvieto, & Florence - 10 Days
Map of Rome, Orvieto, & Florence - 10 Days