- Explore Venice’s canals & grand palaces
- Tour Florence's beautiful medieval piazzas & cathedrals
- Discover the rugged nature and medieval villages of the Cinque Terre
- Enjoy visiting in the Chianti Classico region of Tuscany
- Go back in time to ancient Rome with a tour of the Colosseum
|Day 1||Arrive in Venice||Venice|
|Day 2||Self-Guided City Tour of Venice||Venice|
|Day 3||From Venice to Florence||Florence|
|Day 4||Historic Walking Tour of Florence||Florence|
|Day 5||Drive from Florence to Pisa||Pisa|
|Day 6||Visit Cinque Terre from Pisa||Pisa|
|Day 7||Drive to Siena, stop in San Gimignano||Siena|
|Day 8||Chianti Wine Tasting from Siena||Siena|
|Day 9||Drive from Siena to Rome||Rome|
|Day 10||Vatican Tour: Museums, Sistine Chapel & St Peter’s Basilica||Rome|
|Day 11||Visit the Colosseum & Roman Forum||Rome|
|Day 12||Depart Rome|
Day 1: Arrive in Venice
Welcome to Italy! Arrive in Venice Airport, then transfer to the city center to your hotel. Settle in and spend the rest of the afternoon exploring the city on your own.
Venice in northern Italy is famous for both industry and tourism. With nicknames like "Queen of the Adriatic", "City of Water", and "The Floating City", it's clear that the city's myriad canals are its main draw. Stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea, the city has long been a commercial and cultural hub thanks to its strategic placement. Silk, grains, spices, and art were traded through the Middle Ages, making Venice very wealthy.
The city is also famous for its many beautiful historic attractions, such as the Piazza San Marco and San Marco Basilica, the Grand Canal, and the ornate Doge's Palace. The Lido de Venezia is a popular luxury destination that attracts actors, critics, and other cinema industry celebrities.
In the evening head to the Cannaregio District, site of the former Jewish Ghetto. The area is filled with great restaurants, bars, & shops offering kosher Venetian specialties, a Jewish museum, and several tourist-friendly synagogues. Eat and drink your way through regional specialties as you celebrate your first night in Italy. Buon appetito!
Day 2: Self-Guided City Tour of Venice
We'd recommend starting at the center of it all in St. Mark's Square, or Piazza San Marco. 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.
Admire the impressive Basilica San Marco from outside before venturing in. While admission is free, there is a skip-the-line fee that can be purchased online to avoid lining up in busy months. Be sure to wear appropriate clothing entering inside. Marvel at the incredible mosaics that adorn the inside of the building. If you're up for it, you can climb the campanile, the bell tower of the Basilica that offers incredible views! Here, we'd recommend buying tickets ahead of time online.
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. Most notably, it was the home to the Doge, the ruler of Venice, and the center of government during the Venetian Republic. Before entering for a visit of the incredibly lavish interior of the palace (buy your admission tickets online to save yourself time!), walk over to the Grand Canal side of the palace for a look at another iconic spot in Venice- the Bridge of Sighs. This ornate Baroque-style bridge connected the palace with its first-floor prison and was used to transfer its prisoners.
Having seen the highlights of St. Mark's Square, it's time to make the 10-minute walk to Rialto Bridge. As you explore Venice on foot, you'll surely cross one of the four bridges that span the Grand Canal. The Rialto Bridge is the oldest and arguably most well-known. Linking the districts of San Marco with San Polo, the bridge gives amazing views of both sides of the canal.
A little further down along the Grand Canal you'll find the Rialto Market. This iconic food market is buzzing with local life and flavors. Overlooking the canal, you can stroll around this lively epicenter of daily Venetian life and culture seeing and tasting the local products that make up its incomparable cuisine. Note that the market shuts down around midday and is closed on Sundays and Mondays.
To round out your day, head to another of the four iconic bridges crossing the Grand Canal, the Ponte dell'Accademia. The vantage point from this bridge offers an incredible view of Venice and the canal it spans. Take a moment to admire this picture-perfect setting before heading to a nearby bar to finish off your day with a glass of wine and Cicchetti- the Venetian version of tapas.
Day 3: From Venice to Florence
After breakfast head to the train station to catch a train to Florence. 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, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture.
After settling into your hotel, make the most of your afternoon 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 4: Historic Walking Tour of Florence
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.
Chat with a local specialist who can help organize your trip.
Day 5: Drive from Florence to Pisa
Today, you'll pick up your rental car in Florence and begin the self-drive portion of your exploration of Tuscany. Make your way an hour west to the outskirts of Pisa, where your agrotourism accommodation awaits.
Agriturismo is a style of vacationing that allows travelers a closer look into daily Italian life. The accommodations are typically farmhouses that have been converted to welcome guests. Enjoy this unique experience, escaping the city and enjoying the beauty of the incomparable Italian countryside.
Before heading to your accommodation, stop in the town of Pisa itself, to see the famous Leaning Tower at the Piazza dei Miracoli.
Delve further into the city and nearby spots with other visits to round out your day:
- Dive into history at the Museo Nazionale, the city's most prized museum that features some stunning artifacts and sculptures
- Pay a visit to the Santa Maria della Spina Church, which although small is considered one of Pisa's most beautiful due to its ornate design and riverside location
- Enjoy a cone of gelato or glass of expresso in a streetside cafe neat the Palazzo dei Cavalieri
- Tour the Museo dell’ Opera del Duomo to see a whole host of delightful treasures (bonus - it's one of the least visited in Pisa, so you'll get plenty of time to enjoy everything!)
- Go shopping for high-end luxury items on the historic Borgo Stretto and enjoy beautiful architecture as you browse. The street starts at the Piazza Garibaldi next to the Ponte di Mezzo
- Explore the incredible Pisa Botanical Gardens, the world's oldest university botanical gardens
Day 6: Visit Cinque Terre from Pisa
Head up the coast in your rental car a little over an hour to visit the incredible Cinque Terre, a section of the Italian coast famous for its medieval villages, stunning cliffs, and beautiful hiking trails. We recommend leaving the car for the day in a parking lot in the city of La Spezia, whose train station connects to the five villages of Cinque Terre with an easy access local train.
Today is a free day to explore the area. Select from the following suggestions, then head out to make the most of your time on the sunny coast:
- Soak in the sunshine, sunbathe on the rocks, or dive off the steep cliffs into the turquoise water at one of the Cinque Terre's beaches. The sandy Monterosso Beach has both public and private sections and the Vernazza Beach is rocky and perfect for sunbathing.
- Visit the 17th-century Church of San Francesco to see fine art, including a depiction of the Crucifixion by Antoon Van Dyck and other notable Italian painters of the 17th- and 18th- centuries
- Tour the 1,000-year-old Castello Doria in Vernazza, the Cinque Terre's oldest surviving structure, for sweeping views of the town and harbor
- Climb the Scalinata Lardarina, a steep 377-step staircase that connects the harbor with the village of Corniglia, for some of the Cinque Terre's best views
- Dive into the 14th century at the Chiesa di San Lorenzo, an immersive experience into the art and architecture of that time period
- The Cinque Terre has no shortage of churches—visit a few of them, including the Santuario di Nostra Signora di Montenero in Riomaggiore and the Church of San Giovanni Battista in Corniglia
- Explore the 13th-century Castello Di Riomaggiore, which dominates the Cinque Terre coastline. Built to protect the town from seafaring pirates, the castle is now simply a throwback to a different time, as well as a great place for photographs. Head inside the castle to see the museum exhibit of the centuries of town history
- Walk up to the Torre Aurora, a medieval castle that stands on the intersection of Monterosso's Old Town and New Town
- Pay a visit to Cantina 5 Terre in Riomaggiore, the Cinque Terre's only major winery, to learn about how ancient traditions mix with modern-day production techniques to produce a unique and flavorful wine. Sample the wines, especially the local white, and enjoy a relaxing afternoon
When you're ready, make the drive back to your accommodation near Pisa in the evening.
Day 7: Drive to Siena, stop in San Gimignano
After breakfast, hit the road for the 1.5-hour drive to San Gimignano.
This quintessential village is comprised of medieval buildings perched atop one of the iconic Tuscan hills. Located in the Elsa Valley, the area is known for producing Vernaccia di San Gimignano, a white wine with floral and fruity notes. However, San Gimignano is most famous for the 13th-century walls that encircle it as well as its medieval plazas, churches, and stone towers dominating the skyline. It's for these reasons that the town is a UNESCO World-Heritage Site.
After exploring the village and before continuing on, be sure to pop in at one of San Gimignano's famous gelaterias. They have an earned reputation for producing some of the best gelato in the world.
From San Gimignano, hop back in your car and continue your drive for a quick 45 minutes to the town of Siena, where you'll check into your accommodation. The city's historic center is one of Italy's most famous attractions and is a UNESCO World Heritage Site. Siena is famous for its medieval architecture, museums, and for the Palio, a popular horse race that takes place twice a year in the Piazza del Campo (the main square).
Day 8: Chianti Wine Tasting from Siena
Take the day to continue exploring the Chianti Classico wine region by visiting a typical Tuscan winery. Just a quick drive from Siena in the stunning Tuscan countryside, La Lastra Winery will delight your senses as you learn to savor this region's specialty. The unique characteristics of the local climate have made the region unfavorable to most crops but ideal for growing wine grapes. Soak in the views, as alternating fields of olive orchards and vineyards characterize this idyllic landscape.
The Chianti wine, made primarily of Sangiovese grapes, is the local staple. 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. Tour the cellars and vineyard of this local winery, then enjoy a wine tasting of four regional wines accompanied by local products. End your visit with a light lunch to pair perfectly with your palate.
Head back to Siena for the afternoon and continue to explore the historic center of this timeless town. Visit the city highlights, such as the 13th-century Palazzo Pubblico; the Torre del Magnia, a bell tower with fantastic city views; the green-and-white-striped Duomo; and the Piccolomini Library, which is famous for its soaring Pinturicchio frescoes. Besides these, there's the Museo dell'Opera Metropolitana art museum as well as Siena's many churches, including the Basilica dell' Osservanza, Santo Spirito, and Sanctuary of Santa Caterina.
Day 9: Drive from Siena to Rome
Time to leave lovely Tuscany and make your way to Italy's capital city. After a drive of a little under three hours, you'll find yourself in the incredible center of Rome. We recommend dropping your rental car at the airport, from where a private transfer can take you to your accommodation in the city center.
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.
Take the rest of the afternoon to explore on your own! 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 it from thievery, 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 10: Vatican Tour: Museums, Sistine Chapel & St Peter’s Basilica
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 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 and St. Peter's Basilica. Your guide will help you experience the allure of Renaissance art by divulging secret details and untold stories throughout the tour.
The rest of the day is free for you to explore on your own. Stroll through the Centro Storico, the historic center, of Rome wander past iconic monuments and architecture such as the Spanish Steps and Trevi Fountain. 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.
Day 11: Visit the Colosseum & 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 12: Depart Rome
Time to say goodbye to Italy—for now! After one last Roman breakfast, you'll transfer to the airport for your flight home. Safe travels!