Rome, Orvieto, Florence & Verona - 14 Days

Day 1: Arrive in Rome, Explore

Welcome to Rome! According to legend, Italy's capital was founded by brothers Romulus and Remus in 753 BCE atop Palatine Hill, which you'll have a chance to see in the coming days. As the longtime center of the mighty 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, 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. 

You may want to start at the Catacombs of Priscilla, originally used from the second to fifth centuries as burial grounds for the elite families of Rome. Visitors can see the original structures as well as paintings and artifacts from various periods. Or, simply 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. 

If you have energy left, walk to Colle Aventino, one of Rome's famous seven hills, and Parco Savello (Orange Tree Park), where you can find the renowned keyhole that gives a direct view of the Vatican. This is an excellent place to grab a cappuccino and snack from one of the adjacent cafés. 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: Vatican Tour: Museums, Sistine Chapel & St. Peter's Basilica

After an early breakfast at your hotel, you can visit Vatican City's museums and other top sights during a three-hour guided morning tour. The Vatican is rich in history and art, housing some of the most important Renaissance masterpieces in the world. During the tour, you'll visit the Pio Clementio Museum, 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 personal details and untold stories throughout the tour.

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

Day 3: Self-Guided Visit of the Colosseum & Roman Forum

Dive deep into ancient Rome today with a self-guided visit to the Colosseum and the Roman Forum with an entrance ticket that combines both sites. It's best to start early to beat the crowds, as walking through the Colosseum is like taking a trip back in time to the days of the Roman Empire. Learn about its illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. Keep an eye out for the Arch of Constantine, which was constructed to honor Emperor Constantine's victory in the battle of Milvian Bridge in 312 CE. 

A short walk from here is the Roman Forum, where you'll see excavations dating back 2,000 years that reveal the ruins of temples, squares, religious sites, and other buildings. These were the venues for public speeches, processions, elections, and gladiator matches. Historians and archaeologists refer to the Roman Forum as the most prominent place in world history, and you'll see why as you admire its grounds. 

Complete your self-guided tour of ancient Rome at Palatine Hill, located 131 feet (40 m) above the city. 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. After all this exploring, venture to the nearby Monti neighborhood, less than a 10-minute walk, and tuck into a well-deserved meal.

Day 4: Train to Orvieto, Explore

Spend your last few hours taking advantage of any last activities in Rome before you venture north to Orvieto. This medieval hill town is located in the lesser-explored Umbria region of central Italy, which is easily accessible from both Rome and Florence by frequent trains. The small city is home to a stunning cathedral as well as a network of underground caves built by the Etruscans. 

Upon arrival, make your way to your hotel and take the afternoon to explore the historic center on your own or on a guided tour. If you opt for self-guided exploration, you can climb the Torre del Moro for spectacular views from the hilltop town and the surrounding region. Or, head over to the Pozzo di San Patrizio, a historic well town highlights engineering feat is a marvel designed to obtain water from the bluff's depths.

In the early evening, venture to the edge of town and walk along the city walls to take in your beautiful surroundings in this enchanting place. Then head to the center of the city, where the piazzas come to life with bars and restaurants filled with locals. One notable location is the Piazza della Repubblica, where you can enjoy the atmosphere and settle in for a delicious dinner. 

Day 5: Underground Cave Tour & Wine Tasting

Spend the day exploring Orvieto, starting with a leisurely breakfast at your hotel. Around midday, meet your guide to begin your journey back in time on a two-hour tour of the extensive Underground of Orvieto, made up of more than 400 human-made caves hidden in the cliffside. Created by the inhabitants of the city approximately 2,500 years ago, these caves were used for an array of purposes across the span of Etruscan history.

During the tour, you'll hear stories about this unique geologic wonder as you make your way through a well-lit labyrinth of tunnels, passageways, and caverns. 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 beloved spot nearby for a light lunch and wine tasting. With a lovely view of the cathedral to enjoy while you dine, sample an array of local products such as white wine, cured meats, and cheeses. From here, take the rest of the afternoon to enjoy Orvieto at your own pace.

Day 6: Train to Florence, Explore

After breakfast at your hotel, transfer to the train station for your ride to Florence. Upon arrival, check into your hotel and then set out on foot. Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, the unmissable terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture. 

You might want to start your exploration by walking through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and greenery. You can also visit Chiesa e Museo di Orsanmichele, a church that served as the granary for the Sisters of San Michele in previous years. 

In the evening, stroll around the historic Piazza della Signoria, in front of the Palazzo Vecchio, for some people-watching, followed by dinner and drinks in the trendy Sant'Ambrogio neighborhood.

Day 7: Historic Walking Tour of Florence

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 stop at the iconic Duomo, followed by visits to Giotto's Bell Tower and the Baptistery, with its bronze doors. Your guide will share stories of the famous Renaissance artists who called Florence home.

After your tour, continue exploring on your own. 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 spectacular viewpoint offers an incredible view of all of Florence. It is the perfect place to watch the sunset before heading to Piazza Santo Spirito for predinner aperitivi. 

Day 8: Local Cooking Class in Florence

Enjoy a leisurely morning in Florence with breakfast at your hotel and a slow stroll through the historic center. Popular highlights that you may not have seen yet include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, with its impressive collections of ancient sculptures and paintings. Be sure to purchase your tickets to the Uffizi online to avoid disappointment!

In the afternoon, you'll meet your host near the center of Florence for a traditional Italian cooking class. He or she will first welcome you with a glass of prosecco as you begin the three-hour experience with an appetizer of Italian cheeses and other local products.

Then roll up your sleeves and learn to cook four Tuscan Italian dishes from recipes passed down through generations. Observe the chef's different tricks and techniques 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. No matter what the season is, the best part comes at the end when you and your hosts will sit down and enjoy your freshly-made dinner together.

Day 9: Tuscany Day Trip: Siena & San Gimignano

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

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

Finish the day with a visit to the medieval fortress town of Monteriggioni, perched on a hillside, where you can explore the intact castle walls. Continue to the Chianti Classico wine region to visit a typical Tuscan winery (with tastings!) before returning to Florence for the evening.

Day 10: Train to Verona, Explore

Today you'll leave Florence and make your way up the Italian peninsula to Verona, home of Shakespeare's famous love story. The train journey takes about three hours, with a stop in Bologna. When you arrive, make your way to your hotel to check in before getting out to explore.

An excellent place to start is the Ponte Pietro, the historic arch bridge facing the San Giorgio in Braida Church. From there, venture up the stairs nearby to the Piazzale Castel San Pietro for a stunning view of Verona and a perfect place to watch the sun go down. This centuries-old fortress perched on a hilltop is an impressive architectural wonder in and of itself, but the view it gives of the city below is what makes it so unique. Admire the church towers, river, and city skyline below before returning to the city center. 

Finish the day at Piazza delle Erbe, where you can relax with dinner and a glass of wine amid your beautiful new surroundings.

Day 11: Verona Guided City Tour

After breakfast at your hotel, take a two-hour guided tour of Verona with a local guide. You'll see why this romantic city is more than the setting for the most famous Shakespearean love drama; it is also a UNESCO World Heritage site, and your guide will share information regarding its history and archaeological importance. 

Your walking tour will start with one of Verona's most notable landmarks, the Arena in Piazza Bra (Bra Square). Still used today, this ancient Roman amphitheater is one of the best-preserved of its kind. From there, wander through the cobblestone streets and arrive at the central Bra Square, the largest square in the city and the perfect spot to delve into the importance of ancient economic and political life. 

Nearby, you'll visit the house of Verona's famed lovers and see Juliet's balcony and the Casa di Giulietta, said to have inspired Shakespeare's Romeo and Juliet. Continue your tour and learn why Verona is important in Northern Italy's medieval history. Visit Piazza dei Signori and crisscross through side streets and back alleys as your guide points out the best local cuisine to add to your list of places to try. 

After the tour, take some free time to explore the Roman Theater and Archaeological Museum before crossing the Castelvecchio Bridge, constructed centuries ago in the 1350s. This is where you can visit the Castelvecchio Museum, a small castle and a lovely example of the Gothic architecture of the time. Head back to Piazza Bra in the evening, where restaurants and bars are buzzing with locals and visitors alike. 

Day 12: Day Trip to the Dolomites

Today, set out from the city of Verona to explore the nearby natural wonder of the Dolomite Mountains, which form part of the Southern Limestone Alps and extend from the River Adige to the Piave Valley. This full-day small-group tour takes you by car, giving you the opportunity to admire the views along the way.

Take a moment to breathe in the spectacular view over the Dolomites. After a few hours, you'll enter the Val di Fassa, an expansive valley framed by this impressive mountain range. Enjoy the ride before arriving at Pass Pordoi, at an altitude of 7,345 feet (2,239 m). From here, you'll board a panoramic funicular that reaches more than 10,000 feet (3,048 m), with breathtaking views of the Dolomites. Enjoy some free time to walk around, have lunch, and simply admire your incredible surroundings before heading back to Verona in the evening.

Day 13: Day Trip to Venice

Take advantage of your geographic location today with a self-guided day trip to Verona's neighboring city, Venice. Just an hour away, frequent trains connect the two cities, so you'll have plenty of options to choose from. Once you arrive at the train station, use the city's vaporetto water buses that act as public transportation around the canals of Venice. Start at the center of it all in Piazza San Marco (St. Mark's Square). Take a moment to breathe in the sights and sounds of this famed square before getting a deeper look inside the impressive buildings and architecture that surround it.

Next, admire the impressive Basilica San Marco before exploring the interior and its incredible mosaics. If you're up for it, climb to the top of the campanile, the bell tower of the basilica that offers incredible views. From here, turn your attention to Doge's Palace, also located in St. Mark's Square. This almost 600-year-old building has served many purposes over the course of time but always continued to remain an impressive symbol of Venetian history. Then walk over to the Grand Canal side of the palace for a look at another iconic spot in Venice: the Bridge of Sighs.

Having seen the highlights of St. Mark's Square, it's time to make the 10-minute walk to Rialto Bridge, one of Venice's oldest and most well-known bridges, followed by the Rialto Market, an iconic food market that is buzzing with local life and flavors. From Venice's center, venture into the Cannaregio district, admiring the unique, iconic architecture. Cannaregio has plenty of artisanal shops to explore and not to mention a plethora of delicious restaurants and lively bars to stop in for dinner before heading back to the train station to head back to Verona for your last night. 

Day 14: Depart Verona

Say goodbye, or ciao, to Italy for now! If time allows, take a morning stroll around Verona. After breakfast at your hotel—and perhaps one more cappuccino—transfer to the airport for your connecting flight home. Safe travels!

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