Cortona, located about 50 miles south of Florence and 130 miles north of Rome, is rich in Etruscan roots, dating back to the 4th century BC. The streets of Cortona are easy to wander and spectacular views of the valley are readily available. Be warned, however, the climb to the top (although worth every step and gasp for air) is steep!
Most guidebooks will tell you that one day is all you need to explore Cortona. One day is sufficient to hit the highlights. Two days, however, is ideal for digging a little deeper and experiencing some of the real treasures in this town.
WHERE TO STAY
Hotel San Michele. Located inside one of the oldest buildings (formerly a 15th-century palace) in the heart of Cortona. This charming boutique hotel has been restored to reflect its true history and character. The rooms are simple and decorated with traditional antiques, offering some of the most dramatic views of red-tiled rooftops and the Val di Chiana. If arriving by car, follow the signs to the hotel taking you inside the medieval walls. Once you have unloaded your luggage, you will be required to drive back outside the walls for parking.
WHERE TO EAT
Osteria del Teatro. Situated in a 16th-century building, this restaurant takes special care in serving a fine Tuscan menu. Although it may cost a little more than you would expect to pay for lunch, this is an ideal spot for a fabulous regional meal.
If you only have time for one meal in Tuscany, the following recommendation is a MUST.
La Bucaccia. A visit to Cortona is not complete without a meal at La Bucaccia. Read what I had to say about this restaurant in another post. If you are fortunate to have time for two meals in Cortona, make La Bucaccia your dinner destination. It is romantic, delicious, and most memorable.
WHAT TO DO
Morning: From Piazza della Republica, follow Via Santucci up the hill toward Church of Santa Margherita. The path is steep, but if you take it slowly, you'll catch a glimpse of real life in this town. At the top of the hill, the beautiful chiesa awaits. On occasion, the church's organist performs for those stout enough to conquer the hill. The square in front of the church offers a spectacular view of the Val di Chiana and Lake Trasimene. On the way down, stop in Church of San Francesco, famous for its 13th-century artifacts.
Afternoon: Stroll the small streets stemming from Piazza della Republica. The small boutique shops offer a nice variety of local products including leather, ceramics and art. Some of my favorites are Il Pozzo (gallery of Tuscan photography), Molesini Market Enoteca (wines and olive oils), and Busatti (fine Tuscan linens).
Bonus: If you choose to stay more than one day, discover the world of pecorino cheese in a cheese-making class at La Bucaccia--a truly unique experience that only those in-the-know try!