Tours and Trips in Siena

Discover more of Tuscany on a half-day trip to Siena, located just 45 miles (75 km) south of Florence. With convenient round-trip transport and a private guide, you avoid the stress of navigating on your own and learn more about Siena than you could from a guidebook. In the company of your small group, cap off the tour with an intimate wine tasting of two regional grape varieties.

Spend the day exploring Siena and Chianti on this full-day excursion from Florence. Traveling with a small group ensures you'll get personalized attention from your guide and plenty of time to ask questions. Enjoy the intimate atmosphere that comes with traveling in a group of just 15 people or fewer while exploring the market town of Greve, the hilltop town of San Gimignano, and the main square in Siena. A stop in a local winery lets you taste the famous Chianti blend and learn how the sangiovese grapes are grown and harvested.

Spend the day in the Tuscan countryside and visit the charming towns of Siena, Pisa, and Greve in Chianti. Discover the historic landmarks of each city including the Leaning Tower of Pisa, the Castle of Monterinaldi, the Piazza del Duomo in Siena, and much more. Take the wine road in Chianti and sample a multitude of local wines as well as olive oil, vin santo, and grappa.

Witness the spectacle of Palio de Siena "” the world's longest running horse race "” from an unrivaled vantage point during a half-day experience in Siena. From a balcony on the San Martino bend, you'll watch horses race through the beautiful streets of Siena and immerse yourself in the vibrant atmosphere of the famous biannual event. Throughout the day, you'll revitalize with beverages and appetizers, and watch a traditional medieval parade that celebrates the ancient origins of the Palio de Siena.

Spend a day sipping one of Italy's top wines, Brunello di Montalcino, on this unique trip from Siena. Led by an expert guide, travel to the cellars to learn about the production process and meet the locals behind the delicious red wine. Then, pause at a family-run winery for an authentic Tuscan lunch before exploring the village of Montalcino and the abbey of Sant'Antimo. Stop for additional tastings along the way and conclude with transportation back to Siena. Group size is reserved to eight people for a more intimate experience.

Experience Siena and the Chianti region on this 7.5-hour evening excursion, departing from Florence. Bypass the daytime crowds and arrive in Siena in the late afternoon to explore the Piazza del Campo. From there, visit a Tuscan wine cellar in the famous region of Chianti and enjoy a 4-course meal paired with local wines. After a romantic evening in the Tuscan countryside, you will return to central Florence.

The magnificent Duomo of Siena is one of the highlights of Siena's UNESCO-listed historic center, but its popularity means that you could spend a long time queuing outside. This skip-the-line ticket ensures priority entrance and offers access to the Cathedral, the Piccolomini Library, the Baptistery of San Giovanni, the museum, and the Crypt.