Both are Tuscan hilltop towns. Cortona has Frances Mayes. Montepulciano has Vino Nobile.
Plan your trip →600m elevation. Valdichiana views to Trasimeno. Etruscan museum, Fra Angelico. "Under the Tuscan Sun" tourism. More compact, slightly more crowded.
Renaissance palazzi on the Corso. Piazza Grande. Contucci’s free wine cellar. Vino Nobile DOCG. More elegant, slightly less touristy.
Cortona: Etruscan history, views, literary connection. Montepulciano: wine, Renaissance architecture, Pienza+Val d’Orcia proximity. Wine lovers: Montepulciano. View lovers: Cortona.