This scenic eight-day tour through Italy checks off two world-class cities and a UNESCO-listed hill town in the Umbrian countryside. First, stay three nights in Rome to see ancient ruins and the Vatican's many museums (including the Sistine Chapel). Then pick up a car and drive through the rolling olive groves and wineries to get to medieval Assisi, the birthplace of 12th-century St. Francis. Finish the adventure in Florence, where you'll discover elegant gardens and Renaissance masterpieces.


  • Let a private guide teach you about the Roman Empire during a full-day tour
  • Drive to olive groves and wineries (with tastings!) in lesser-known Umbria
  • Get your feet wet in Florence with a walking tour through the historic center
  • Walk along Assisi's impressive castle, built as a fortress along the town walls

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome, Explore Rome
Day 2 Walking Tour of the Colosseum & Roman Forum Rome
Day 3 Self-Guided Vatican City Experience Rome
Day 4 Pick Up Rental Car & Drive to Assisi, Explore Assisi
Day 5 Umbria Wine Tasting & Olive Oil Tour Assisi
Day 6 Drive to Florence, Explore Florence
Day 7 Historic Walking Tour of Florence Florence
Day 8 Depart Florence  

Detailed Itinerary

Day 1: Arrive in Rome, Explore

Walk around Centro Storica to see elegant squares like the Piazza Navona

Welcome to Rome! According to legend, Italy's capital was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill. As the longtime 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 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. 

Perhaps you want to start at the Catacombs of Priscilla, which were originally used from the 2nd to 5th centuries as burial grounds for the elite families of Rome. Visitors can see the original structures as well as paintings and artifacts from various time periods. Another good idea is to 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.

You can also head to the Colle Aventino, one of Rome's famous seven hills, and Parco Savello (Orange Tree Park), where you can find the famous keyhole that gives a direct view of the Vatican. This is a good place to grab a cappuccino and snack from one of the adjacent cafés. Or, 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: Walking Tour of the Colosseum & Roman Forum

The Roman Forum
Your private guide will show you around the Roman Forum

Dive into the history of the Roman Empire today with a walking tour of the Colosseum, the world's largest amphitheater. Learn about the lives of some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperor Augustus, Nero, and the Flavian Emperors who built the Colosseum. 

From here, continue to the Roman Forum, where you'll see excavations dating back 2,000 years which reveal the ruins of temples, squares, religious sites, and other buildings. These were the venues for public speeches, processions, elections, and, of course, gladiator matches. Historians and archaeologists refer to the Roman Forum as the most celebrated place in world history, and you'll see why as you admire its grounds. You'll also cut through the Roman Forum along Via Sacra to pass by the Temples of Vesta, Antonino, and Faustina. 

Your tour of ancient Rome ends 131 feet (40 m) above the city at Palatine Hill. 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. In the evening, continue exploring more of Rome on your own. Perhaps you want to grab dinner in one of the city's other neighborhoods, such as the bohemian Monti or upscale Prati, with an abundance of Art Nouveau architecture.

Day 3: Self-Guided Vatican City Experience

Consider starting early at the Vatican to beat the crowds

After an early breakfast at your hotel, take the entire morning to visit the Vatican and St. Peter's Basilica at your own pace. Make sure to give yourself 4-5 hours total to see everything these famous sites have to offer. Start by entering the Vatican Museums, of which there are dozens. 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. There will likely be a line here, so give yourself an hour or so to go through the process of this once-in-a-lifetime experience. If you're not part of a tour, you'll be made to exit the Sistine Chapel outside, where you can line up again to enter St. Peter's Basilica. This wait can vary but allow yourself 1-2 hours to queue up and visit the main church. 

The rest of the day is free for you to explore on your own. Stroll through more of Rome's historic 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 some pizza, gelato, and people-watching.

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Day 4: Pick Up Rental Car & Drive to Assisi, Explore

Spend two nights in the UNESCO-listed town of Assisi

Enjoy one last Roman breakfast at your hotel before you make your way north on a self-guided road trip. First, pick up your rental car and then drive through a lesser-visited region of Italy, Umbria, which is known for its stunning landscapes and hilltop towns. Umbria is also home to the charming town of Assisi, two hours from Rome, where you'll stay for the next few nights. Birthplace of St. Francis and home to the incredible Basilica di San Francesco, Assisi is sure to charm you as soon as you arrive. 

The entire town is a UNESCO World Heritage site, so take the afternoon to explore its impressive medieval architecture on your own. Start by visiting Rocca Maggiore, an impressive castle built as a fortress along the town walls, located high above the town. Wander around its unique architecture and take time to soak in the impressive views it offers of the Umbrian valley below. In the evening, head to the stunning main square of Assisi, Piazza del Comune, to feel the town come to life as you pop into a nearby osteria or trattoria for dinner.

Day 5: Umbria Wine Tasting & Olive Oil Tour

Visit olive groves and wineries in the Umbria region

There are two main staples in Italian culture and diet: wine and olive oil. Today you'll take a half-day tour to explore all that goes into the production of these two regional delights of Umbria while soaking in the stunning beauty of the region.

Your tour starts at a local vineyard, where you'll learn about the grape cultivation process and the cultural tradition of winemaking that has been passed down through the generations in Italy. Then it's time to taste! You'll tour the wine cellar and learn how best to pair these local wines with regional products in this picture-perfect setting. From there, head to an authentic oil mill to observe the milling process firsthand from an Umbrian producer. You'll then taste for yourself their most well-known extra virgin olive oils.

In the afternoon, return to Assisi and continue exploring at your own pace. A good option for your last afternoon here is the Roman Forum and Museum. This underground area has been excavated to give visitors a glimpse at past Roman life, with a temple, a large cistern, statues, and other ancient artifacts.

Day 6: Drive to Florence, Explore

Florence's iconic skyline is peppered with terracotta rooftops

Today it's time to hop back in your rental car and make the 2.5-hour journey north to the city of Florence. Once you arrive, you can drop off your rental car and make your way to your hotel to check in. Settle in and take the rest of the afternoon to explore this incredible city, truly a capital of culture, at your leisure.

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome that's impossible to miss, and the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture. To start, you might consider heading to Studio Artesia, located steps away from the Ponte Vecchio, to learn more about ancient fresco painting techniques. Alternatively, walk through the peaceful Boboli Gardens to see an oval-shaped island called Isolotto, surrounded by various sculptures and greenery.

In the evening, make your way around the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for some people-watching, followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 7: Historic Walking Tour of Florence

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 make a stop at the iconic Duomo, followed by visits to Giotto's Bell Tower and the Baptistery, with its bronze doors. Finish at the Galleria dell'Accademia, where your guide will share stories of the famous Renaissance artists who called Florence home.

After your tour, continue exploring on your own. Perhaps you want to spend a few hours at the Uffizi Gallery, one of Europe's best art museums. Or 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 viewpoint offers an incredible view of Florence and is the perfect place to watch the sunset before you head over to Piazza Santo Spirito for predinner aperitivos

Day 8: Depart Florence

Take one last look at the Duomo before departing

Say goodbye, or ciao, to Italy for now! Take advantage of any free time this morning with one last walk through the streets of Florence. At the appointed hour, you'll transfer to the airport to catch your flight home or to your next destination. Safe travels!

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Map of Rome, Assisi & Florence - 8 Days
Map of Rome, Assisi & Florence - 8 Days