Ascoli Piceno Dominated by mountains leading up into the Apennines, this medieval and Renaissance town features a charming piazza (Piazza del Popolo) dominated by a Gothic church and 13th-century town hall. In August the Giostra dell Quintana--a medieval jousting tournament--is held in the old town.
Urbino In the 15th century, the court of Urbino, led by Federico da Montefeltro, was one of the most illustrious in Europe. His Renaissance palace, the Palazzo Ducale, is extraordinary and now houses the Galleria Nazionale delle Marche. Urbino is also a lively university town, hosting the Urbino Jazz Festival in June and the International Festival of Ancient Music in July.
Parco Nazionale dei Monti Sibillini Ancient legends relate that an enchantress awaits in her cave for the unwary and the devil has turned a lake red with his blood in this magical mountainous park. Medieval towns remain tucked away in the shadows of the mountains. Castles and lookout towers that once offered protection against Saracen raids dot the hillsides. This is gorgeous hiking country with abundant wildlife and precious spring and summer wildflowers.
Grotte di Frasassi It's been said that the Milan cathedral could fit into this enormous cave--one of Europe's biggest. Spectacular stalagmites and stalactites are 1.4 million years old.
Macerata An untouristy, 10th-century hill town, Macerata has a lively university and hosts the annual Stagione Lirica, one of Italy's most spectacular outdoor venues, attracting world-class opera stars and performers.
San Leo In an impressive setting made famous by Dante in his Divine Comedy, this 15th-century fortress is the best in Marche