Hugged by Cypresses, Olive trees and Elms is the ancient castle of Penna San Giovanni, which commands jaw dropping views across the sinuous hills and beautiful countryside of Le Marche. Visit the lovely churches, the oldest being La Pieve di San Giovanni Battista (the Church of St. John the Baptist- after whom the town is named), which was completed in 1256 or enjoy watching live music and dramas at the elegant early 19th century theater, constructed in wood. If you happen to come here in the summertime then you can witness several famous events including the Festa della Polenta. Located at the top of the town, is a small park from where you can feast your eyes to spectacular views of the Marches and on a clear day the Adriatic is also visible. If you are a true nature lover then Penna San Giovanni is the perfect place for you. Go hiking over the mountains, plunge in the crystal clear waters of the lakes, and spot the exotic animals and birds at the splendid Conero National Park. In the winter, the town gets covered with a thick sheet of snow and becomes a perfect place for enjoying winter sports like skiing, snowmobiling, and sledging. And if you seek a dose of culture and history then you can hire a car and from your Penna San Giovanni accommodation, drive down to the medieval towns of Fermo, Amandola, Loreto and Ascoli Piceno.

Penna San Giovanni is known for its wonderful food and the local wines that are traditionally served in quaint restaurants and cafes. Owing to its proximity to Penna San Giovanni villa rentals and homes, these fine dining establishments are thronged by hordes of vacationers throughout the year. The town has several shops where you can buy all essentials, from fresh fruits and vegetables to bakery items to colorful clothing and lovely handicrafts. Drop by the lively bars where you can your senses to the region's finest wines and other alcoholic spirits and also savor hot piping pizzas, and authentic Italian ice-creams.