Tuscany Self-Drive Tour - 8 Days
Highlights
- Explore Florence's beautiful medieval architecture
- Hike between coastal villages in Cinque Terre
- Sip wine in the Chianti Classico region of Tuscany
- Sleep in an "agriturismo" (farm stay) in the Italian countryside
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Arrive in Florence, Explore | Florence |
| Day 2 | Historic Walking Tour of Florence | Florence |
| Day 3 | Pick Up Rental Car, Drive to Pisa & Explore | Pisa |
| Day 4 | Day Trip to Cinque Terre | Pisa |
| Day 5 | Day Trip to Lucca | Pisa |
| Day 6 | Drive to Siena via San Gimignano | Siena |
| Day 7 | Chianti Wine Tasting Tour | Siena |
| Day 8 | Return to Florence, Depart |
Detailed Itinerary
Day 1: Arrive in Florence, Explore
Welcome to Florence, the capital of the Italian region of Tuscany. Transfer from the airport to the city center and check in at your hotel. Spend some time relaxing and settling in, then head out for a relaxing stroll and dinner downtown. Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Cathedral of Santa Maria del Fiore (frequently referred to simply as the Duomo for its striking terracotta-tiled dome) and the Galleria dell'Accademia, home to Michelangelo's celebrated "David" sculpture.
After walking through the central Piazza del Duomo, visit the Mercato Centrale, a 19th-century open-air market, to browse a wide selection of vegetables, fruits, meats, and cheeses. Then take a stroll through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by sculptures and greenery. In the evening, explore the historic Piazza della Signoria, located in front of the Palazzo Vecchio. Go for dinner and drinks in the hip Sant'Ambrogio neighborhood before getting some rest at your hotel.Day 2: Historic Walking Tour of Florence
Spend the day exploring the city on a guided half-day walking tour. Follow your guide through the picturesque historic center, where you'll find the most important squares and monuments, including Piazza della Repubblica and Palazzo Vecchio. Soak up the architecture and the atmosphere before heading over to the Ponte Vecchio, the historic bridge spanning the Arno River. Later, stop at the Duomo, Giotto's Bell Tower, and the Baptistery. Finally, enter the Galleria dell'Accademia to see Michelangelo's masterpiece.
After your tour, continue your exploration of Florence on your own. Head across the Arno to visit Piazzale Michelangelo, a spectacular viewpoint offering an incredible view over Florence. It's the perfect place to watch the sunset before heading to Piazza Santo Spirito for aperitivi (predinner drinks and snacks).
Day 3: Pick Up Rental Car, Drive to Pisa & Explore
Today, you'll pick up your rental car in Florence and begin the self-drive portion of your exploration of Tuscany. Drive to the town of Pisa to see the famous Leaning Tower at the Piazza dei Miracoli. There's plenty more to see in Pisa: delve into history at the Museo Nazionale, visit the Santa Maria della Spina Church, prized for its ornate design and riverside location, and have a gelato in a café near Palazzo dei Cavalieri. Tour the Museo dell' Opera del Duomo or shop for luxury souvenirs on the historic Borgo Stretto.
Explore the incredible Pisa Botanical Gardens, the world's oldest university botanical gardens, to finish the day. Then you'll get back in your rental car and drive to the outskirts of Pisa, where your agritourism accommodation awaits. Agriturismo accommodations are usually farmhouses that have been converted to welcome guests. Enjoy this unique experience, enjoying the beauty of the incomparable Italian countryside, over a relaxing dinner.
Day 4: Day Trip to Cinque Terre
Make the hourlong drive up the coast to visit the incredible Cinque Terre, a section of the Italian coast famous for its medieval villages, stunning cliffs, and beautiful hiking trails. Leave the car in a parking lot in La Spezia, then catch a local train to any of the Cinque Terre's five villages. There are so many ways to enjoy this picturesque region. Hike the trail that leads you through all five villages, 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.
Visit the 17th-century Church of San Francesco or the 1,000-year-old Castello Doria, the Cinque Terre's oldest surviving structure, for sweeping views of Vernazza and its 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. Explore the 13th-century castle known as Castello Di Riomaggiore, or visit Cantina 5 Terre in Riomaggiore, the Cinque Terre's only major winery, for a wine tasting. In the evening, make the drive back to your accommodations near Pisa.
Chat with a local specialist who can help organize your trip.
Day 5: Day Trip to Lucca
Another day trip awaits you today. You'll visit Lucca, a city with Etruscan and Roman history. Lucca's medieval fortification walls are still intact; they're used as a walking and biking path that circles the city center. Stop into 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, the Complesso Museale della Cattedrale, and the 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). Alternatively, you could rent a bike and explore the city center or go horseback riding on the bike paths along the Serchio River. At the end of the day, drive back to your accommodations near Pisa.
Day 6: Drive to Siena via San Gimignano
After breakfast, hit the road for the 1.5-hour drive to San Gimignano. This charming village comprises medieval buildings perched atop one of the iconic Tuscan hills. A UNESCO World Heritage Site, San Gimignano is most famous for its 13th-century walls, medieval plazas, churches, and stone towers dominating the skyline. The larger area of the Elsa Valley is known for producing Vernaccia di San Gimignano, a white wine with floral and fruity notes.
Before driving onward, pause for a sweet treat: San Gimignano is said to produce some of the best gelatos in the world. Then hop back in your car and continue on a 45-minute drive to the town of Siena, where you'll check into your accommodation. The city's historic center, one of Italy's most famous attractions, is a UNESCO World Heritage Site. Go for an evening stroll through the Piazza del Campo, the main square.
Day 7: Chianti Wine Tasting Tour
Enjoy the first part of the day exploring the Chianti Classico wine region by visiting a 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 Chianti wine, made primarily of Sangiovese grapes, is the local staple. 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 lunch and a wine tasting of four regional wines.
Head back to Siena for the afternoon and explore the historic center. Visit highlights such as the 13th-century Palazzo Pubblico, the Torre del Magnia bell tower, the green-and-white-striped Duomo, and the Piccolomini Library, famous for its Pinturicchio frescoes. Other cultural attractions include the Museo dell'Opera Metropolitana art museum and Siena's many churches, including the Basilica dell' Osservanza, Santo Spirito, and the Sanctuary of Santa Caterina. Enjoy a leisurely Tuscan-style dinner on the last night of the trip.
Day 8: Return to Florence, Depart
After one last cappuccino over breakfast, it's time to say goodbye and drive back to Florence to return your rental car and catch your flight. Safe travels!
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