Explore Tuscany's incredible art and history with this itinerary. Start your trip in Florence, where world-famous works by Michelangelo, da Vinci, and others dominate the art scene. On a self-drive tour, explore the Tuscan countryside to see 13th-century churches in Siena and try the renowned Chianti wine. Visit the leaning tower of Pisa and relax in the charming villages of the Cinque Terre before ending your trip back in Florence.


  • Tour Florence's beautiful medieval piazzas & cathedrals
  • Visit the leaning tower of Pisa
  • Discover the rugged nature and medieval villages of the Cinque Terre
  • Tour the medieval cities of Siena & Lucca
  • Enjoy wine tasting in the Chianti Classico region of Tuscany

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Florence Florence
Day 2 Historic Walking Tour of Florence Florence
Day 3 Local Cooking Class in Florence Florence
Day 4 Drive from Florence to Pisa Pisa
Day 5 Visit Cinque Terre from Pisa Pisa
Day 6 Visit Lucca from Pisa Pisa
Day 7 Drive to Siena, stop in San Gimignano Siena
Day 8 Chianti Wine Tasting from Siena Siena
Day 9 From Siena to Florence, Depart Florence

Detailed Itinerary

Day 1: Arrival in Florence

Various cured meats in the Mercato Centrale
Various cured meats in the Mercato Centrale

Welcome to Florence, the capital of Italy's Tuscany region! Arrive at Florence Airport and transfer to the city center to check in to your hotel. Spend the rest of the day relaxing and settling in, or head out for a relaxing stroll and dinner downtown.

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. 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 Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats and cheeses, and a variety of lunch spots  
  • 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 

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

Day 2: 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 3: Local Cooking Class in Florence

Learn How to Make Traditional Italian Pasta
Learn How to Make Traditional Italian Pasta

Enjoy a leisurely morning in Florence, with breakfast at your hotel and a few slow strolls through the historic center. Popular highlights include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, which houses works by artists like Michelangelo and Leonardo de Vinci. Be sure to purchase your tickets to the Uffizi online in advance!

In the afternoon, you'll meet your host near the center of Florence for a traditional Italian cooking class. They'll welcome you with a glass of prosecco. Enjoy the venue as you begin the experience with an appetizer of Italian cheeses and other local products.

Next you'll roll up your sleeves and learn to cook regional Italian pasta from recipes passed down through generations. Your hands-on Italian cooking class will last about three hours. You'll learn to cook four dishes from scratch, including a side or dessert. Observe the chef's different tricks and techniques involved 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. 

The best part of the class is at the end, where you'll enjoy your freshly-made dinner in a traditional Italian style, shared with your hosts.

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Day 4: Drive from Florence to Pisa

Leaning Tower of Pisa
Leaning Tower of 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 5: Visit Cinque Terre from Pisa

Monterosso's picture-perfect beach.
Monterosso's picture-perfect beach.

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 6: Visit Lucca from Pisa

Main square of Lucca

Today, head out in your rental car to visit Lucca, a city whose founding goes back to the Etruscans and Romans. Lucca's medieval fortification walls are still intact and are now used as a walking and biking path that circles the city center. 

Explore the city with these recommended activities: 

  • Visit the 12th-century Chiesa e Battistero di San Giovanni e Santa Reparata, a Catholic church in the Piazza San Giovanni
  • Explore art and history at the Museo Nazionale di Palazzo Mansi,  Complesso Museale della Cattedrale, and Lucca Center of Contemporary Art 
  • Tour the beautiful English-style landscaped gardens of the Parco della Villa Reale di Marlia, the home of Elisa Bonaparte—Napoleon's sister 
  • Rent a bike and explore the city center and the city walls 
  • Go horseback riding on the bike paths along the Serchio River
  • Learn about the Italian composer Puccini and the connections to his hometown in a concert series

When you're ready, head back to your rental car and make the drive back to your accommodation near Pisa. 

Day 7: Drive to Siena, stop in San Gimignano

Brick houses in Siena
Brick houses in Siena

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

Wine tasting

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: From Siena to Florence, Depart

Florence Duomo
Florence Duomo

After one last cappuccino over breakfast, it's time to say goodbye and make the one hour drive back to Florence to catch your international flight. Make sure to arrive at the airport with a little extra time to hand over your rental car!


Map of Tuscany Self-Drive Tour - 9 Days
Map of Tuscany Self-Drive Tour - 9 Days