1. Breakfast at hotel. || 43.772977946346934, 11.249711183409644
2. 7:45 AM - 7:30 PM - Full day in Tuscany on you own (cost not included). || 43.77075013275135, 11.262270617512593
Transfer from hotel to meeting point on your own. Start your Tuscany day trip from Florence by meeting at 7:45 AM at the front of Santa Maria Novella train station, where you’ll board an air-conditioned coach for a scenic 1-hour and 15-minute drive to Siena, one of Tuscany’s most beautiful and famous medieval hilltop towns. In Siena, you'll enjoy a 1-hour guided walking tour through its historic streets, starting at Piazza Salimbeni, home to Monte dei Paschi di Siena, the world's oldest surviving bank, and learning about the city's rich history as a banking town. Then, you’ll stroll through the Contrada della Torre, one of Siena’s 17 districts, or “contrade,” each with its own animal symbol and strong sense of local identity. You’ll also visit the famous Piazza del Campo, the sloping, sea-shell-shaped square where the renowned Palio horse race is held twice a year, and end your walking tour inside the Duomo di Siena, a cathedral known for its intricate marble floor, a masterpiece of over 50 images created over two centuries. After the guided tour, enjoy free time to explore the city at your own pace, whether shopping or relaxing at a café. From Siena, travel for 45 minutes to Fattoria Poggio Alloro, an organic, family-run winery in the Chianti region, where you’ll enjoy a wine-tasting lesson and a traditional Tuscan lunch with homemade pasta, cured meats (prosciutto and salami), local cheeses, a garden salad, and Tuscan biscotti, all paired with wines from the estate while soaking in panoramic views of the rolling Tuscan countryside. Next, head to San Gimignano, a UNESCO World Heritage Site and a smaller hilltop town, known for its medieval towers, 14 of which remain from an original 72. Here, you’ll have free time to explore the charming streets, including Piazza della Cisterna (where you can try the world-famous gelato from Gelateria della Piazza), and then visit the Piazza del Duomo, home to the Collegiata Cathedral, which boasts colorful 14th-century frescoes, or climb the Torre Grossa for a bird’s-eye view of the town. Afterward, head to the Rocca of Montestaffoli, a peaceful fortress with olive trees and breathtaking views of San Gimignano’s towers. Finally, make your way to Pisa for a 1-hour and 30-minute scenic drive through the Tuscan countryside, where you'll arrive at the iconic Piazza dei Miracoli, home to the Leaning Tower, the cathedral, baptistry, and monumental cemetery. You’ll have about an hour to explore these monuments and, if you choose, climb the Leaning Tower for stunning views of the square and beyond (strongly recommended to pre-book tickets for this to skip the line). The tour concludes with a 1-hour drive back to Florence, leaving you with a camera full of pictures, a belly full of delicious Tuscan food and wine, and memories of one of the most scenic and historic regions of Italy.
3. Free time
4. Night in Florence