Concierge.com's insider take:
Dominating the fertile Valdichiana from a rocky spur, this handsome medieval walled town used to be a fairly recherché stop on the Tuscan tourist map, but Frances Mayes' bestsellers Under the Tuscan Sun and Bella Tuscany changed all that (Mayes' country house is nearby, and Cortona features prominently in both books). Cortona is now one of the most densely touristed small towns in Tuscany, but away from peak times, it absorbs the influx well—and it's easy enough to get away from the madding crowd by heading to the quiet and picturesque upper town. Be sure to check out the clock tower on the Palazzo Comunale and the view of Val di Chiana that opens off Piazza del Duomo. In the piazza, the Museo Diocesano (1 Piazza del Duomo; 39-0575-62-830) features Beato Angelico's inspiring Annunciation, while the state-of-the-art MAEC museum gives an overview of Cortona's rich history from prehistory through Etruscan and Roman times to the present day, and displays the collections of the Accademia Etrusca—the world's oldest archaeological academy, founded in 1727 (9 Piazza Signorelli; 39-0575-630-415; www.cortonamaec.org). Perhaps the most beautiful walks and drives around Cortona, though, are beyond the town itself. As it's set on the border between Tuscany and Umbria, venturing afield will give you a taste of both. Madonna del Calcinaio, a Renaissance church with pure, serene lines, rises at the foot of town on the road to Camucia. Follow the country road out of Cortona from the Porta Colonia for two miles to reach the mystical Convent of Le Celle, founded by St. Francis between 1211 and 1221—it's still home to Franciscan monks, who silently welcome visitors to the saint's cell dug into the rock.