Travel south from Florence into Tuscany's rolling hills. Begin with free time in Siena, where you can explore Gothic streets, admire Piazza del Campo, and view the Duomo from the outside. Pause at the Medici Fortress for panoramic countryside views.

Continue into the Chianti region for a true Tuscan experience. Visit a family-run winery for a guided tasting of 5 wines, including Chianti Classico and Super Tuscan varieties. Enjoy a traditional lunch featuring truffle lasagna, cured meats, pecorino cheese, crostini, and homemade dessert.

Finish the day in San Gimignano, a medieval hilltop town famed for its towers and charming streets. Explore artisan shops and picturesque alleys at your own pace. Before returning to Florence, treat yourself to award-winning gelato from one of the most renowned gelaterias in the world.