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The lovely hill towns of Arezzo and Cortona serve as introductions to the region. They carry on age-old local traditions—each September Arezzo's beautiful Romanesque and Gothic churches are enlivened by the Giostra del Saracino, a costumed medieval pageant. Since ancient times, Arezzo has been home to important artists: from the Etruscan potters who produced those fiery-red vessels to the poet Petrarch and the writer, architect, and painter Giorgio Vasari. Cortona, magnificently situated, with olive groves and vineyards creeping up to its walls, commands sweeping views over Lago Trasimeno and the plain of the Valdichiana. The delightful medieval streets are a pleasure to wander, and the town has two fine galleries and a scattering of churches that are worth a visit.
Plan on spending a good four days to tour the area. Arezzo and Cortona each merit a full day, and if you stay in the vicinity you'll have a good base from which to explore the countryside. Both towns are close to the A1 (Autostrada del Sole) and are on main train lines.
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