Florence 1587 Tours & Activities

Pisa, Siena, San Gimignano, Chianti and Monteriggioni Small-Group Tuscany Day Trip

Start with a hotel pickup from central Florence, or meet your driver-guide in Piazza della Repubblica. Hop inside your air-conditioned minivan, and gaze out of the window as you travel through Tuscany, where tiny towns cling to verdant hills and cypress trees dot the landscape.

After just over an hour on the road, stop in Siena, the region’s second largest city that once rivaled Florence for power and wealth. On a walking tour, visit Piazza del Campo, a glorious square that’s the hub of the city and site of the annual Palio di Siena horse race. Striking in appearance, the square is home to a collection of architectural dazzlers including Palazzo Comunale, the towering Torre del Mangia and Siena Duomo. After exploring, use some free time to visit the monuments independently, if you wish.

From Siena, journey past the vineyards and olive groves of Chianti to the fortified hamlet of Monteriggioni, a gem of a town built during the 13th century. Take a walk around its still-intact medieval walls, admiring its handsome 11 towers.

After soaking up the sights, return to Chianti and stop at a sprawling country estate for lunch. Feast on Tuscan staples such as lasagne or seasonal ribollita — a hearty Tuscan soup made with cannellini beans, tomatoes and vegetables — plus local pecorino cheese, cold cuts of salami and finocchiona (Tuscan salami), and bruschetta (roasted bread with olive oil). Pair your meal with a tasting of fine Chianti and vernaccia wine (see selection below) as you learn all about this prestigious local wine from the friendly owner of the estate.

After you top off lunch with dessert wine and almond biscuits, spend your afternoon in the nearby hill town of San Gimignano, with a UNESCO-listed Old Town that’s famous for its medieval ‘skyscrapers.’ Take a stroll through the center to discover a cluster of architectural jewels: Piazza della Cisterna, Palazzo del Podestà, the Church of Sant Agostino and a collegiate church that’s known as the ‘dome of San Gimignano.’
Before returning to Florence, enjoy a final visit to Pisa for a walk around Piazza dei Miracoli, home to the legendary Leaning Tower of Pisa as well as Pisa Duomo, the baptistery and monumental graveyard. Make the most of your last stop to pose for all-important photos by the tower, and then sit back and relax, enjoying last looks of the Tuscan countryside, before a drop-off either in central Florence or at your hotel.
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Pisa, Siena, San Gimignano, Chianti and Monteriggioni Small-Group Tuscany Day Trip
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