Experience the delights of Tuscany’s rolling hills as you tour enchanting towns, vineyards and ancient fortresses. Take in the beautiful town of San Gimignano with its hundred towers, the ancient fortress of Monteriggioni, the spectacular views of the Val d’Orcia and the sprawling vineyards of Montalcino. On the route, you will stop off at traditional wineries to sample the delicious local meats, cheeses and of course, the Chianti wines for which this region is so famous. Begin the day with a trip to San Gimignano, a stunning hilltop town with its stone towers and picturesque medieval squares. Your tour guide will explain the town’s rich history and culture and then leave you free to explore the narrow streets and squares for yourself. Be sure to browse the many artisan shops that occupy the old stone houses. From here you will head to Monteriggioni, the ancient crown-shaped fortress that adorned the head of Italy on the old 100 lire currency. The same walls, which date back to the 13th century, are home to 14 towers that Dante likened to the Giants of Inferno in his Divine Comedy. After a brief visit, relax at a Chianti winery for a lunch of salami, cheeses and other local products, accompanied by a tasting of the local wines. Admire the views of the Val d’Orcia´as you proceed to Montalcino, the hilltop town that stands above 1500 hectares of Brunello vineyards. Take the opportunity to visit a local wine cellar to sample the world-famous local vintage and taste other typical Tuscan delicacies.