Start your day at 7:45 AM by boarding a fast-speed train to Florence (tickets included). Upon arrival, head to the "P" parking sign in Piazza della Calza near Porta Romana to meet your guide at 9:45 AM for a 10:00 AM departure. Begin your journey through the stunning Chianti countryside, soaking in views of rolling hills, vineyards, and cypress trees. The first stop is a charming winery, where you'll enjoy a tasting of four wines paired with balsamic vinegar, truffle oil, and olive oil. Next, visit a second winery just 5 km from San Gimignano. Explore the estate, taste three more wines—including Chianti Colli Senesi and a rosé—and admire the breathtaking Tuscan landscape. Your final stop is San Gimignano, the "Medieval Manhattan." Spend 1.5 hours wandering cobblestone streets, visiting landmarks like Piazza del Duomo, and enjoying local treats. Return to Florence by 5:00 PM, then take the train back to Rome, arriving by 8:00 PM.