On the drive to Siena, take in the steep Tuscan countryside. You'll see Piazza del Campo, home to the towering Torre del Mangia and the historic Palazzo Comunale, site of the annual Palio horse race. You'll have free time to explore the Cathedral and the narrow streets.
From Siena, you'll take a panoramic road through vineyards and olive groves in the heart of Chianti to a pleasant country estate surrounded by aromatic plants, you'll have a lunch based on typical Chianti products and a tasting of fine Chianti and Vernaccia wines, explained by the farm owner.
After lunch, you'll visit San Gimignano, another UNESCO World Heritage Site, which earned the nickname "Manhattan of the Middle Ages" for its still-standing medieval city walls and towers. You'll learn about genuine works of art like the Church of Sant' Agostino, the Dome, the Piazza della Cisterna, and the Palazzo del Podestà.
Once in Pisa, enjoy the sight of Piazza dei Miracoli, where the peerless masterpieces in marble rise in the green lawn: the Leaning Tower, the Baptistery, the Cathedral, and the Monumental Graveyard, the ultimate expression of the Romanesque architecture of the twelfth and thirteenth centuries.