Starting from Florence, the journey takes you to Cortona, one of the most ancient and charming villages in Tuscany. Perched on a hill in the Val di Chiana and made famous by the movie Under the Tuscan Sun, Cortona boasts Etruscan origins, evidenced by the imposing walls surrounding it, which date back to the 4th century BC. The village offers a perfect blend of medieval architecture, authentic atmospheres, and local culture, making it an unmissable destination for those seeking timeless beauty and authenticity.

The next stop is Montepulciano: in this captivating Renaissance town, you’ll have the opportunity to taste the prestigious Nobile di Montepulciano wine in a charming and historic underground cellar, learning the secrets of its production and having the chance to purchase bottles at attractive prices. After the included tasting, you’ll have free time for lunch (not included) at a typical trattoria and to explore the beauties of the historic center, famous as the set for films like New Moon and the series Medici: Masters of Florence featuring Dustin Hoffman and Richard Madden.

As you continue toward the Val d'Orcia, you will enter the heart of one of Tuscany’s most scenic areas, where you can admire the iconic landscapes of rolling hills dotted with cypress trees, known worldwide for their ineffable beauty and recognized as a UNESCO heritage site. Along the way to Montalcino, you will spot the settings of famous films like The Gladiator—a perfect opportunity for taking iconic photos.

The final stop is Montalcino, a charming hilltop town surrounded by the rolling landscapes of the Val d’Orcia. Known worldwide as the home of Brunello, one of Italy’s most prestigious wines, Montalcino offers an authentic taste of Tuscan tradition, history and beauty. Enjoy its medieval atmosphere, scenic views and deep connection to local wine culture.