Siena and San Gimignano with Dinner at the Winery - Full-Day Tour - Florence

Join this small group tour to explore the stunning sights of Siena, San Gimignano, and the beautiful Chianti countryside. Relax in the warm evening light and conclude your day with a traditional Tuscan dinner at a scenic winery.

In ancient times, Siena was the only city in Tuscany that competed with Florence for power, wealth, and artistic beauty. You will depart from Florence and travel comfortably in a luxury air-conditioned minibus, accompanied by an English-speaking driver and tour leader.

In Siena, enjoy a guided walking tour through the heart of this charming city. Discover the magnificent Piazza del Campo, where the famous Palio horse race is held every year, and wander through the quieter medieval streets while learning about the Contrade, the 17 historic districts that passionately compete in the Palio.

Next, the journey continues to San Gimignano, known for its medieval towers, fortified walls, and winding alleys that capture the essence of Tuscan hill towns. With its unique skyline and hilltop location, San Gimignano offers unforgettable views and a timeless atmosphere. You’ll have some free time here to explore, take photos, or simply soak in the surroundings.

Tuscany is also famed for its culinary heritage, and after visiting both Siena and San Gimignano, you’ll enjoy a local tasting of traditional products—a flavorful break that adds another layer of authenticity to your afternoon.

As the afternoon gently turns to evening, you'll be welcomed at an elegant Chianti winerysurrounded by vineyards and rolling hills. Visit the estate’s ancient cellars and learn about the wine production process, then settle in for a typical Tuscan dinner paired with the winery’s finest labels. The setting and ambiance will make this moment one of the most memorable parts of your journey—an authentic, relaxed, and delicious experience in the Tuscan countryside.

This wonderful itinerary leaves your morning free while offering a complete immersion into the highlights of Tuscany’s landscape, towns, food, and wine—all in the intimacy and comfort of a small group setting.