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. Finish 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
  • 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 Early Morning Vatican Experience Rome
Day 3 From Rome to Orvieto Orvieto
Day 4 Underground Tour & Wine Tasting in Orvieto, onto Florence Florence
Day 5 Historic Walking Tour of Florence Florence
Day 6 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. 

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

Day 2: 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.

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Day 3: From Rome to Orvieto

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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. 

Day 4: Underground Tour & Wine Tasting in Orvieto, onto Florence

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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 man-made caves used for an array of purposes across the span of Etruscan history. Travel back in time as you hear the stories before your guide takes you to a locally adored spot nearby for a light lunch and wine tasting. With a lovely view of the Duomo, enjoy a sampling of local products before saying goodbye to this lovely city. 

Make your way to the train station to catch an afternoon train into Florence. Once arrived at the station, you'll head to your hotel and settle in for the evening.  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 5: 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.

In the evening, head over to the trendy Piazza Santo Spirito for some pre-dinner aperitivos

Day 6: 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 - 6 Days
Map of Rome, Orvieto, & Florence - 6 Days