Pisa, Siena & San Gimignano Day Trip with Lunch & Wine Tasting, Florence

Your day begins with an early departure from Florence, where you'll join your small group of fellow travelers aboard your vehicle and head south to your first stop (just over an hour away). Siena is a beautifully preserved medieval city known for its 13th-century redbrick buildings and narrow, steep streets. Following your guide, you'll be led through the brick-lined historic center to discover the city's shell-shaped Piazza del Campo, home to the renowned Palio, an annual bareback horse race, and learn about the traditions that still shape life in the city today.

Next, continue to the hilltop town of San Gimignano, nicknamed the "Manhattan of the Middle Ages" (or "Medieval Manhattan") for its distinctive skyline of medieval towers. Enjoy free time to wander its cobblestone streets, browsing artisan shops (perhaps picking up a ceramic souvenir or two), and admiring the historic architecture—Piazza della Cisterna is a good place to start for a concentration of medieval structures, and for impressive panoramas of the surrounding countryside? Climb the Torre Grossa tower. Midday, sit down to lunch on classic Tuscan dishes paired with wines, spotlighting the region's offerings.

In the afternoon, you'll travel onward to Pisa, your final stop. Here, you'll explore the green-lawned Piazza dei Miracoli, a UNESCO-listed site (the third of the day) that's home to the cathedral, baptistery, and, of course, the world-famous Leaning Tower—one of Italy's most recognizable landmarks. Take time to admire the Romanesque architecture, capture photos, and, if the lines are short, purchase tickets on-site to climb the unintended tilted bell tower. As the day comes to a close, relax on the return journey to Florence and reflect on a day spent experiencing the art, history, and landscapes that define Tuscany.