Private San Gimignano & Siena Day Trip with Lunch, Florence

Your day begins with a hotel pickup in Florence, where your private driver welcomes you aboard a comfortable vehicle for a scenic 90-minute transfer into the Tuscan countryside. Leaving the city behind, you'll listen to your driver share insights into the region's landscapes, traditions, and villas and estates as the verdant vineyard-lined hills, olive groves, and historic villas unfold along your route.

Your first stop is the hilltop town of San Gimignano, a UNESCO-listed gem often called the "Town of Towers" for its distinctive medieval skyline. You'll have time to explore at your own pace—strolling cobbled streets, browsing artisan shops, and admiring the preserved architecture that defines this historic village before meeting up with your driver a few hours later to return to the countryside and onward to a typical Tuscan winery not far from San Gimignano.

You'll sit to a traditional meal paired with regional wines, sampling local vintages as you overlook the restored estate—originally a convent—and surrounding vineyards and farm for a glimpse into rural Tuscan life. With full bellies, your driver will next bring you to Siena, another UNESCO-protected city, renowned for its 13th-century redbrick buildings and narrow, steep streets, shell-shaped Piazza del Campo, and the centuries-old Palio di Siena, an annual bareback horse race. Then, when it's time, you'll pile into the vehicle for your final transfer back to Florence, noting the light changing over the Tuscan hills.

With your driver providing context as you drive, your visits to San Gimignano and Siena are explored independently. Yet, for those seeking more in-depth knowledge, a private guide can be arranged to accompany you throughout the day.