Monteriggioni is a medieval walled town, located on a natural hillock, built in 1214–19. During the conflicts between Siena and Florence in the Middle Ages, the city was strategically placed as a defensive fortification.

Wine Tasting and Tuscan Lunch with authentic local cuisine included. Upon arrival the guests are greeted by their host for a brief walking tour of the historic property.

San Gimignano is a small walled medieval hill town. Known as the Town of Fine Towers, San Gimignano is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, with its hilltop setting and encircling walls form "an unforgettable skyline". Within the walls, the well-preserved buildings include notable examples of both Romanesque and Gothic architecture, with outstanding examples of secular buildings as well as churches. The "Historic Centre of San Gimignano", is a Unesco World Heritage Site.