Nestled between two stunning cities, the town of Assisi makes for the perfect stopover for your journey up the Italian peninsula. With a couple of days to explore these stunning landscapes of the Umbria region with your rental car, this tour visits the highlights of Rome and explores the Renaissance beauty of Florence, combined with a few nights of small-town Italian life.


  • Go back in time to ancient Rome with a tour of the Colosseum
  • Explore the lesser-known and stunning Umbria region of Italy
  • Tour Florence's beautiful medieval piazzas & cathedrals
  • Enjoy a wine tasting in the Umbrian region

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome Rome
Day 2 Visit the Colosseum & Roman Forum Rome
Day 3 Self-Guided Vatican City Visit Rome
Day 4 Drive from Rome to Assisi Assisi
Day 5 Assisi Walking Tour & Afternoon Visit of Spello Assisi
Day 6 Umbria Wine Tasting and Olive Oil Tour Assisi
Day 7 Drive from Assisi to Florence Florence
Day 8 Historic Walking Tour of Florence Florence
Day 9 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: Visit the Colosseum & Roman Forum

The Roman Forum
The Roman Forum

Dive into the history of the Roman Empire 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. 

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 archeologists refer to the Roman Forum as the most celebrated place in world history, and you'll see why as you admire its grounds.

Cut through the Roman Forum along Via Sacra, where you'll pass by the Temples of Vesta, Antonino, and Faustina. Also here is the Basilica Julia and Aemilia, a public meeting house that was commissioned by Julius Caesar.

Your tour of ancient Rome ends 131 feet (40 meters) above the city at Palatine Hill. From here you'll have incredible views of the city, with the Forum on one side, Circus Maximus on the other, and the Vatican in the distance. In between, the River Tiber snakes through Rome's historic neighborhoods.

In the evening, you'll have free time to continue exploring Rome. Grab dinner in one of the city's other neighborhoods, such as bohemian Monti or upscale Prati, which is brimming with art nouveau architecture.

Day 3: Self-Guided Vatican City Visit

St. Peter's Square and the Vatican

Take the day to visit the Vatican and St. Peter's Basilica on your own. Altogether, we recommend giving yourself 4-5 hours total to see everything these famous sites have to offer. You'll start your self-guided visit entering the Vatican Museums. 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. These vast halls hold one of the world's largest art collections, so be sure to take your time to visit, usually about 2-3 hours. 

Continue through the museums to the Raphael Rooms, where you can admire the frescoes before entering the incredible Sistine Chapel. The line here can be a bit of a wait, so give yourself an hour or so to line up, walk through, and visit and your pace. 

Only being part of a tour will allow you to go directly from the Sistine Chapel at the end of your visit to the Vatican museums into Saint Peter's Basilica. 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 about 1-2 hours in case of a wait and to visit the main church. 

Keep in mind that it's a one-way visit through the Vatican museums- so take your time exploring at your pace instead of rushing to the Sistine Chapel, as you won't be able to head back after.

Day 4: Drive from Rome to Assisi

View of Assisi from above
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Today it's time to say goodbye to Italy's capital and head north. Head to pick up your rental car before starting your drive up into a lesser-visited region of Italy- Umbria. Equally stunning in its landscapes and hilltop towns, Umbria is home to the charming town of Assisi, just two hours away from Rome. 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. We recommend heading to Rocca Maggiore, an impressive castle built as a fortress along the town walls, located high above the town. Explore 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 trattoria for dinner.

Day 5: Assisi Walking Tour & Afternoon Visit of Spello

Hilltop town of Assisi

Renowned as a pilgrimage destination in Italy as the birthplace of Saint Francis, Assisi contains a wonder of medieval streetscapes to explore. Take the morning to experience Assisi with a walking tour to hear about the rich history that made the town into the marvel that it is today.  See for yourself the incredible Basilicas of Saint Chiara and Saint Francis and the artworks they hold, and tour the maze of cobblestone streets with your expert guide. 

In the afternoon, why not venture over to the nearby village of Spello? Just a 20-minute drive down the road, this little gem is home to a yearly flower festival that fills the place with incredible color. Take a couple of hours to explore it's postcard-worthy streets and plaza, before heading back to your accommodation in Assisi for the evening.

Day 6: Umbria Wine Tasting and Olive Oil Tour

Wine tasting in the Umbria region

There are two main staples in the Italian culture and diet: wine and olive oil. Take a half-day to explore all that goes into the production of these two regional delights of Umbria. You'll visit a winery and olive grove and soak in the stunning beauty of the region as you delve deeper into the process and history of both winemaking and olive oil production.

After learning about the grape cultivation process and the cultural tradition of winemaking that has been passed down through the generations in Italy, it's time to taste! You'll tour the wine cellar and learn how best to pair these local wines with regional products before sampling the wines in this picture-perfect setting.

From there, head to an oil mill to observe the milling process firsthand from a local producer. You'll then taste for yourself their most well-known extra virgin olive oils.

In the afternoon, continue to explore Assisi on your own. Make your way to the Roman Forum and Museum, this underground area has been excavated to give visitors a glimpse at past Roman life, showcasing the base of the temple, a large cistern, statues, and other ancient artifacts.

Day 7: Drive from Assisi to Florence

Florence skyline

Today it's time to hop back in your rental car and make the 2.5-hour journey up 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 at your leisure. 

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 Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years
  • 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 8: Historic Walking Tour of Florence

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

Spend the day exploring the city's top sites, starting with a guided half-day walking tour. 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 explore the beautiful squares and architecture that make Florence so picturesque. Soak in the atmosphere before heading over to the Ponte Vecchio, where you can admire the Arno River.

You'll then make a stop at the iconic Duomo, with its terracotta-tiled dome, where across the way Giotto's Bell Tower and the Baptistery with its bronze doors create an unforgettable scene. Finally, with Skip the Line entrance tickets in hand, you'll head to the Galleria dell’Accademia to see Michelangelo’s David. Your guide will share stories of Michelangelo and how this masterpiece came to be.

After your tour, continue your exploration of Florence on your own.  Head across the Arno River to visit to Piazzale Michelangelo. It's a bit of an uphill climb or a quick taxi ride away. This spectacular viewpoint offers an incredible view 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 9: 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, Assisi, & Florence - 9 Days
Map of Rome, Assisi, & Florence - 9 Days