Ascoli Piceno, the capital of the province of the same name, is one of the most beautiful small towns in Italy. It is the southernmost province of the Marche region, with an interior that is 60% hilly and mountainous. The most famous coastal towns are San Benedetto del Tronto, Grottammare and Cupra Marittima. Many of the inland hill towns are characterized by a small but very picturesque historic centers.
Province of Ascoli Piceno travel guide
Ascoli Piceno

Ascoli Piceno is the capital of the province. The town is dominated by a central square (Piazza del Popolo), surrounded by a medieval district with narrow streets and many stores. Famous attractions include the Sant’Emidio Cathedral, the Palazzo del Capitano del Popolo and the many city towers.
San Benedetto del Tronto
San Benedetto del Tronto is the main town of the so-called Riviera delle Palme, a stretch of coastline that includes Grottamare and Cupra Marittima. Although the town boasts some beautiful churches as well as museums, it is primarily a summer vacation destination. Consequently, the beach of San Benedetto has been highly rated for many years.
Nature
The only flat part of the province is the coast line, a strip of about 20 kilometers. The further inland one travels, the more mountainous the region becomes. The highest mountain is called Vettone and it is almost 2,500 kilometers tall. The most famous nature reserves are the Monti Sibillini National Park and the Gran Sasso National Park.