Meet your English-speaking driver at your hotel on a comfortable Mercedes-Benz to start the journey to the beautiful Cortona. Enclosed by stonewalls dating back to Etruscan and Roman times, Cortona sits on the top of a hill. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. The town has become very popular in the past decade thanks to the book by Frances Mayes, Under the Tuscan Sun (and the film with Diane Lane) which is set in Cortona. You will have time to relax or explore the area, the driver will suggest the best things to do in the area.

Leave at 11:30AM for have a delicious light lunch at a family winery. Continue then to Montepulciano on a relaxing 30 minute drive on the hills surrounded by breathtaking landscapes. Of course your driver can stop the car at anytime you want if you wish to take photos.

Arrive at the charming Montepulciano around 2:00PM. This is a medieval hill town of rare beauty full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners. Montepulciano has received lots of attention following the filming of the vampire saga Twilight sequel New Moon here and has seen a notable increase in visitors. A walk through Montepulciano is the best way to view the town as well as enjoy stunning views of the surrounding countryside covered by vineyards producing the famous Nobile which is possible to taste in the many wine shops located within the city's walls.