Discover the history of medieval Tuscany with a visit to two of the most famous medieval locations in Italy, Siena and San Gimignano. Along the way, you will taste delicious local food and drink and even enjoy lunch at a wine estate. You’ll depart from Rome to visit Siena, one of the best-preserved medieval cities in Europe, distinguished by its ancient brick buildings. The fan-shaped central square, Piazza del Campo, is known throughout the world for the famous Palio, a historical horse race that is still run today.  While exploring such historic sites, try an Italian coffee and taste some of the typical pastries of Siena: the Panpepato, the Panforte, and the Ricciarelli.  From Siena, you will continue to San Gimignano, known as The Town of Fine Towers. You’ll soon see why, with its absolutely unforgettable skyline featuring a dozen well-preserved tower houses. Explore its charming medieval streets and feel like you’ve stepped backward in time.  You’ll then stop for a wine tasting and enjoy local delicacies in a beautiful local winery. From there, it’s a visit to the local estate to learn how the grapes are processed. Finally, you’ll enjoy a fantastic lunch at the estate's restaurant before returning to Rome.