San Gimignano, Chianti, and Montalcino Day Trip from Siena

Start with a 7:30am or 8:30am hotel pickup, depending on the time of year. As the sights of Siena slip into the distance, you’ll notice the landscape turn into the undulating hills of Tuscany.

Your first stop in the region is the beloved hill town of San Gimignano, a UNESCO World Heritage Site. Enjoy free time here to wander the streets of its historical center, gazing at the medieval architecture, towers, piazzas, and artisan shops. San Gimignano produces the renowned vernaccia wine, and you’ll find plenty of enoteche (wine shops) around the streets.

Next, you’ll head to the historic fortress town of Monteriggioni. The hill town is encircled by intact medieval walls, beautifully preserved from the 12th century. Hear how Dante likened the walls’ towers to the Giants of Inferno in his Divine Comedy as you enter the town, then make your way to a winery for lunch. Savor a light meal of local cheese and salami, paired with Chianti wine.

With your appetite sated, you’ll travel into the Val d’Orcia region of Tuscany where the winemaking village of Montalcino awaits. Taste the esteemed Brunello di Montalcino wine, and learn about the town’s winemaking traditions.

Relax on the journey back to Siena, and finish your day trip with a hotel drop-off.