Arrival. In the afternoon meet your local guide for a walking tour in the jewel of Tuscany. Cortona, birth place of famous artists as Luca Signorelli and Pietro da Cortona. Characterized by its medieval palazzi and small streets Cortona also offers amazing views over and beyond the Valdichiana and to the monte Amiata. Dinner and overnight.

Breakfast. Today you will enjoy a full day excursion starting from a guided visit of Città della Pieve, birthplace of Perugino, one of the most famous Italian Renaissance painters. In the Cathedral admire an altarpiece by Perugino and right in the Chapel get astonished by one of his masterpieces “The Baptism of Christ” (16th century). The layout of Citta della Pieve was completed around the 13th century and has been preserved almost intact over the centuries. The town plan has important and interesting symbolic meanings - in fact it looks like an eagle, the symbol of Emperor Frederick II, who died in 1250. Lunch in a local restaurant. In the afternoon, en route back to Cortona, enjoy a moment of relax at the Outlet Village Valdichiana. Overnight.

Breakfast. Today will enjoy an extraordinary Tuscan experience. Fall in love with the rolling landscapes, the colours and fragrances on your way to Montalcino. Savour Italy’s most famous wines during a winery visit and tasting at Frescobaldi’s Castelgiocondo, followed by a genuine lunch. Return to Cortona and overnight.