From the Sistine Chapel in Rome to Michelangelo's 'David' in Florence, this trip is perfect for travelers who want to see Italy's top sights at a relaxed pace, while getting a glimpse at a more off-the-beaten-path region as well. Start in Rome for trendy wine bars, nighttime foodie crawls, and a visit tour of Vatican City, end in Florence to explore the medieval cathedral and plazas. Nestled between the two big cities is the lesser-visited and equally stunning region of Umbria, where you'll stop to admire the landscapes to round out your trip. 

Highlights

  • Explore the world-famous Vatican Museum and Sistine Chapel
  • Discover ancient legends and Rome's darker side at the Colosseum
  • Soak in the tradition and culture as you tour the Rome's top cultural sites
  • Explore the lesser-known and stunning Umbria region of Italy
  • Tour Florence's beautiful medieval piazzas & cathedrals

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome Rome
Day 2 Self-Guided Visit of the Colosseum and Forum Rome
Day 3 Early Morning Vatican Experience Rome
Day 4 From Rome to Perugia Perugia
Day 5 Full Day Winery Visits and Tastings near Perugia Perugia
Day 6 From Perugia to Florence Florence
Day 7 Florence Self-Guided City Tour Florence
Day 8 Tuscany Day Trip: Siena & San Gimignano Florence
Day 9 Local Cooking Class in Florence 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: Self-Guided Visit of the Colosseum and Forum

The Colosseum
The Colosseum

Dive into the history of the Roman Empire with a self-guided visit to the Colosseum, the world's largest amphitheater. Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. Learn about some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. 

As you approach the Colosseum, you will see the Outer Wall with 3 levels of arches. Near the Colosseum, stands the Arch of Constantine which was constructed to honor Emperor Constantine’s victory in the battle of Milvian Bridge in 312 AD. The Colosseum, the Roman Forum, and the Palatine Hill are all located very close to each other in the same archaeological area. 

Recommended Schedule

Best to start early in the morning! Give yourself 2-3 hours to visit the Colosseum- with a little extra time to go through security- and around 1 -2 hours to explore the Roman Forum & Palatine Hill. 

While many rush to visit the Colosseum first, the Palatine Hill is typically the least crowded of these three sites and offers an entrance with shorter lines. As it's not the typical order to visit- it might a good idea then to start your visit bright and early here. As you walk through Palatine Hill, make your way to the directly connected and incredible Roman Forum. Your entrance ticket serves for all three sites, so after making your way through the Roman Forum to see the impressive monuments, the exit will lead you right next to the entrance of the Colosseum. 

Day 3: Early Morning Vatican Experience

St. Peter's Square and the Vatican
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 tour will start early at the Vatican, entering the Museums at 8 am and giving you a one-hour head start on the rest of the crowds. See the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps. 

Continue on to the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel to see Michelangelo's Genesis ceiling frescoes and his Last Judgement altar fresco. Finally end the tour at St. Peter's Basilica and Square and experience the magic of Renaissance art as you learn about the secret details and untold stories of the masterpieces. 

The rest of the day is free for you to explore on your own. Stroll through the tangle of narrow streets in Centro Storico, one of Rome's most historic districts, to see classical Roman and baroque architecture. 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. In the evening, why not go for a stroll in the buzzing Monti neighborhood, an eclectic area in the city center full of hip wine bars and trendy boutiques.

Day 4: From Rome to Perugia

Perugia, in the Umbria region

Discover the lesser-explored Umbria region of central Italy. Easily connected to both Rome and Florence by frequent trains and equidistant between these two larger cities, Perugia makes for the perfect stop to compliment your travels. With its hilltop location and medieval architecture, the city is also home to one of Italy's oldest universities as well as an annual chocolate festival and summer jazz festival- giving it a new fresh vibe of cafes and boutiques to explore. 

From Rome, set out by train for a 2-hour ride into Umbria. Once you arrived in Perugia, make your way to your nearby hotel on your own. Take the afternoon to explore the historic center on your own or with a guided tour. 

Often overshadowed by some famous nearby neighboring towns in Tuscany, the Etruscan and medieval city of Perugia is one of Italy's most underrated. You'll feel one with the locals as you stroll amongst the ancient architecture and explore its many plazas, alleys, and archways. Venture to the Piazza IV Novembre in the center of the city to get a feel for the city's enchanting atmosphere. Time seems to stand still as locals sit on the steps of the Gothic-style Cathedral of the plaza to soak up the sun or have a drink with friends, surrounded by centuries-old architecture. 

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Day 5: Full Day Winery Visits and Tastings near Perugia

Wine tasting

Today, take a full day to discover the stunning landscapes and the surrounding area of ​​the Umbria region. Your private car and driver will pick you up in the morning as you delve deeper into one of the region's (and country's) specialty- wine!

You'll be driven through the hills of Umbria and enjoy the incredible views before arriving at the first vineyard. Walk through the vineyards as you learn about the history and culture of the Sagrantino wines and the traditions passed down over generations.

Today you'll visit three wine cellars to learn about the specific grapes and vines cultivated in the region as well as the entire process of wine production.
From the vine to the glass, you'll see firsthand all that goes into every bottle and the culture carried with it over time. 


And of course, taste for yourself! Your tour will include several tastings of wines at each cellar as well as pairings of local products and snacks along the way. When it's time to head back, your driver will take you back to Perugia in the late afternoon. 

Day 6: From Perugia to Florence

Florence skyline

Make your way to the train station to catch an afternoon train from Perugia into Florence. Once arrived at the station, you'll head to your hotel and settle in for the evening. 

Florence is Tuscany's regional capital and its most populous city. Long considered a cultural capital and the "Jewel of the Renaissance", Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo and the Galleria dell'Accademia.

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: 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 9: 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 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

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