Meet your guide in front of the church of San Domenico in Siena at 2:30pm, easy to find even if you are arriving from out of town with your own car, as there is parking in the vicinity.Travel north into the Chianti hills where we visit a Chianti wine estate to tour the property’s vineyards and wine cellars and learn about the winemaking process before sitting down to enjoy a tasting of the famous Chianti Classico Black Rooster wines. Walk around Monteriggioni, a medieval and perfectly preserved fortress with a complete ring of city walls and turrets built in the 13th century and mentioned by Dante. Continue to the world heritage site and "Hill Top Town of Towers" San Gimignano, just as the day’s large crowds and strong light begin to dwindle. Visit this beautiful and romantic Town of Towers at a leisurely pace, enjoying personal time to see the Collegiata church with its chapel dedicated to the local Saint Fina, or marvel at Sienese and Florentine art in the Civic museum. Browse the many boutique shops of artisanal goods such as leather and hand painted pottery, or sample local products in the food and wines stores, particularly the local saffron and Vernaccia wine for which the town is known. Take a walk up to the Rocca fortress to marvel at the surrounding views or spend your time exploring the town’s many hidden beauties. After working up an appetite walking the medieval streets of San Gimignano, head out of town to a farm and enjoy a full Tuscan dinner with tastings of local wines. Weather permitting, dinner will be served outdoors.