Make your way to three of Italy's most famous cities by train and rental car on this 11-day adventure. You'll land in Venice, the "Floating City," with time to wander through its network of 150 canals. Then take a train to Florence to see Renaissance masterpieces and elegant gardens. This is where you'll begin your road trip through Tuscany, visiting hill towns, wineries, and villages on the Mediterranean. Continue the journey to Rome, where ancient history and eclectic neighborhoods await.


  • Explore Venice's charming network of canals and islands at your own pace
  • Take a walking tour in Florence that ends with Michelangelo's "David" 
  • Spend a day with views of the Mediterranean Sea while in the Cinque Terre
  • Drive through Tuscany, visiting medieval hill towns and wineries in Chianti
  • Visit the Vatican's museums, including the Sistine Chapel, with a private guide

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Venice, Explore Venice
Day 2 Venice Self-Guided City Tour Venice
Day 3 Train to Florence, Explore Florence
Day 4 Historic Walking Tour of Florence Florence
Day 5 Pick Up Rental Car, Drive to Pisa Pisa
Day 6 Day Trip to the Cinque Terre Pisa
Day 7 Drive to Siena via San Gimignano Siena
Day 8 Chianti Wine Tasting Tour Siena
Day 9 Drive to Rome, Explore Rome
Day 10 Vatican Tour: Museums, Sistine Chapel & St. Peter's Basilica Rome
Day 11 Depart Rome  

Detailed Itinerary

Day 1: Arrive in Venice, Explore

Venice's main waterway is the picturesque Grand Canal

Welcome to Italy! Upon arrival in Venice, you'll transfer to the city center and check in at your hotel. Get settled and then spend the rest of the afternoon exploring the city at your own pace. Located in northern Italy, Venice 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. Due to its strategic placement, Venice has long been a commercial and cultural hub, stretching across 117 small islands in the marshy Venetian Lagoon along the Adriatic Sea

The city is famous for its many beautiful historical attractions, such as Piazza San Marco (St. Mark's Square) and Grand Canal. Before you experience these highlights, consider taking a gondola to a lesser-visited neighborhood called the Cannaregio District, the site of the former Jewish Ghetto. The area has great restaurants, bars, and 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: Venice Self-Guided City Tour

St. Mark's Square is adjacent to the Basilica San Marco

After a good night's sleep, it's time to explore Venice on a self-guided tour, starting with St. Mark's Square. Take a moment to breathe in the sights and sounds of this famed plaza before getting a deeper look inside the buildings and architecture surrounding it. One such place that will likely grab your attention is the impressive Basilica San Marco. Enter early in the day to marvel at the incredible mosaics before the crowds, and if you're up for it, climb the bell tower that offers stunning views. Just make sure to wear appropriate clothing (no bare arms or bare legs). 

From here, turn your attention to Doge's Palace, also in St. Mark's Square. This almost 600-year-old building has served many purposes over 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. Then walk over to the Grand Canal side of the palace to 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—one of the four scenic bridges that span the Grand Canal. A short walk from here brings you to the buzzing Rialto Market. Stroll around this lively epicenter of daily Venetian life and culture, tasting local products that help create the city's incomparable cuisine. Continue walking along the Grand Canal and then sit at a bar and order a glass of wine and cicchetti (the Venetian version of tapas).

Day 3: Train to Florence, Explore

Florence is the birthplace of the Italian Renaissance period

After breakfast in Venice, it's time to catch a train to Florence, Tuscany's regional capital and most populous city. Long considered Italy's cultural capital and the "Jewel of the Renaissance," Florence is home to many masterpieces of art and architecture.

Once settled at your hotel, make the most of your afternoon by visiting iconic sights, like Studio Artemisia, steps away from the Ponte Vecchio, to learn about ancient fresco painting techniques. You can also visit the Chiesa e Museo di Orsanmichele, which served as the granary for the Sisters of San Michele in previous years. If the weather is nice, walk through the peaceful Boboli Gardens, surrounded by various sculptures and lots of greenery.

In the evening, continue on foot to the La Terrazza Continentale for a predinner cocktail on the terrace while you enjoy the sunset. Then make your way to the Sant'Ambrogio neighborhood for dinner with a glass of Tuscan wine.

Day 4: Historic Walking Tour of Florence

Florence's historic center is compact and 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 stop at the iconic Duomo to see the terra-cotta dome, followed by visits to Giotto's Bell Tower and the Baptistery, with its bronze doors. Finish the tour at the Galleria dell'Accademia to see Michelangelo's "David" while your guide shares stories of the artist and how this masterpiece came to fruition.

After your tour, continue exploring Florence on your own. 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 and is the perfect place to watch the sunset before heading to Piazza Santo Spirito for predinner aperitivos

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Day 5: Pick Up Rental Car, Drive to Pisa

The Leaning Tower is not the only attraction in 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 agritourism accommodation awaits. This style of farmhouse allows travelers to experience a closer look into daily Italian life while enjoying the beauty of the countryside. 

But first, before heading to your accommodation, spend the day in Pisa itself to see the famous Leaning Tower at the Piazza dei Miracoli. There's more to the city, though, including museums like Museo Nazionale, Pisa's most prized museum that features some stunning artifacts and sculptures. A lesser-crowded option is the Museo dell' Opera del Duomo to see many delightful art treasures. Also worth a visit is 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.

When hungry, sit at a streetside café near Palazzo dei Cavalieri for lunch, followed by a cone of gelato or a shot of espresso. In the afternoon, you can shop for high-end luxury items on the historic Borgo Stretto and enjoy beautiful architecture as you browse. You could also while away a few hours at the incredible Pisa Botanical Gardens, the world's oldest university botanical gardens.

Day 6: Day Trip to the Cinque Terre

Monterosso's picture-perfect beach.
Hike between villages or relax on Monterosso's picture-perfect beach 

This morning, head up the Ligurian coast in your rental car to visit the incredible Cinque Terre, a section of the Italian beach famous for its handful of medieval villages, stunning cliffs, and beautiful hiking trails. It's a good idea to leave your car for the day in a parking lot in La Spezia, whose train station connects to all five villages of Cinque Terre, making it a cinch to get around.

Perhaps you want to sunbathe on the rocks or dive off the steep cliffs into the turquoise water at one of the Cinque Terre's beaches. The expansive and sandy Monterosso Beach has public and private sections, while Vernazza Beach is rocky and perfect for sunbathing. For some of the best views, climb the Scalinata Lardarina, a steep 377-step staircase that connects the harbor with the village of Corniglia.

You can also 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. Another castle is 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 and a great place for photographs. Head inside the castle to see the museum exhibit of the centuries of town history. 

Other highlights include Cantina 5 Terre in Riomaggiore, the Cinque Terre's only major winery, where you can learn 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, return the train to your car in La Spezia and return to your accommodation near Pisa in the evening.

Day 7: Drive to Siena via San Gimignano

Explore this UNESCO-listed hill town before driving to Siena

After breakfast, it's time to hit the road for the 1.5-hour drive to San Gimignano. This quintessential village comprises 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. For all these reasons, the town is a UNESCO World Heritage Site.

After exploring the village, be sure to pop in at one of San Gimignano's famous gelaterias, as the town has earned a reputation for producing some of the best gelatos in the world. Then hop back in your car and continue to another UNESCO-listed destination, Siena, where you'll check into your accommodation. The city's historic center is one of Italy's most famous attractions, with medieval architecture and museums. Check out where the Palio is held, a famous horse race that takes place twice a year in the main square, Piazza del Campo.

Day 8: Chianti Wine Tasting Tour

Drive to the beautiful vineyards near Siena and taste Chianti

Take the day to explore the Chianti Classico wine region by visiting a typical Tuscan vineyard. 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 winery, then enjoy a wine tasting of four regional wines accompanied by local products. End your visit with a light lunch before returning to Siena. 

In the afternoon, you can continue to explore Siena's historic center. Visit the city highlights, such as the 13th-century Palazzo Pubblico and the Torre del Magnia, with a scenic bell tower. You can also walk to the green-and-white-striped Duomo and the Piccolomini Library, famous for its soaring Pinturicchio frescoes. Besides these, there's the Museo dell'Opera Metropolitana art museum and Siena's many churches, including the Basilica dell' Osservanza, Santo Spirito, and Sanctuary of Santa Caterina

Day 9: Drive to Rome, Explore

Walk through Centro Storico to see Piazza della Rotonda and the Pantheon

It's time to leave lovely Tuscany and go to Italy's capital city. After a drive of a little under three hours, you'll finish your road trip to the Eternal City: Rome. A good idea is to drop your rental car at the airport and take a private transfer 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 longtime center of the mighty 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. Perhaps you 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, paintings, and artifacts from various 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.

Next, head to the Colle Aventino, one of Rome's famous seven hills. Then continue to Parco Savello (Orange Tree Park), where you can find the renowned keyhole that gives visitors 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 10: Vatican Tour: Museums, Sistine Chapel & St. Peter's Basilica

St. Peter's Square and the Vatican
Take a guided tour of Vatican City before the afternoon crowds

This morning you can visit Vatican City's museums and other top sights during a three-hour guided tour. The Vatican is rich in history and art, housing some of the most important Renaissance masterpieces in the world. 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 secret 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 11: Depart Rome

Until next time, Rome!

Time to say goodbye, or ciao, to Italy for now! After one last Roman breakfast, you'll transfer to the airport for your flight home. Safe travels!

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Map of Discover Venice, Tuscany & Rome - 11 Days
Map of Discover Venice, Tuscany & Rome - 11 Days