Journey to Assisi, birthplace of St. Francis, and admire the Basilica of San Francesco and Piazza del Comune. Enjoy lunch on your own, but make sure to save room for dessert and wine tasting later in day after traveling to Perugia. There, you can take in the sights of the old town center on a sightseeing tour of the Fontana Maggiore, the Gothic Cathedral, and the Rocca Paolina.  

After spending the morning in picturesque Todi, journey to Orvieto, where you will visit the Etruscan Necropolis. This magnificent Gothic cathedral includes the Chapel of San Brizio, frescoed by Fra Angelico, and Signorelli's masterpiece, The Last Judgment. After admiring these timeless works of art, take a step back in time on a stroll through the medieval town center.

Leave the Umbrian hillside behind and travel to Montepulciano, a Renaissance town located atop a limestone ridge in Tuscany. This town, known world wide for its wine, sets the perfect scene for exploring the beautiful wine cellars of the Renaissance Cantina Redi, also known as the Cathedral of Wine. You will also have time to visit the Temple of San Biagio & Piazza Grande while there.