High on the hills bordering the Marches and Romagna, Gradara is both the first and most important stronghold in the province of Pesaro bosting some 14 towers, a beautiful internal portico, a stunning staircase and magnificent frescoed banqueting and reception halls. In medieval times the ill-fated love affair between Paolo Malatesta and Francesca da Polenta was immortalized by the great poet Dante Alighieri in his Divine Comedy (Inferno, Canto V). Pesaro, the second largest city in the Marches is dominated by the castle which stands majestic right in the center of the city. The Rocca Costanza, a massive square building with four huge towers, surrounded by a wide ditch, is situated just a few blocks away from Casa Rossini, the house where one of Italy’s greatest composers – Gioacchino Rossini was born; the annual Rossini Opera Festival in August has earned a world-wide reputation for performing works from his large repertoire of bel canto operas. Pesaro is a peaceful little city, and its seaside promenade and historic center can quite happily be explored on foot or by bike. Among the city's most significant works of architecture are the Palazzo Ducale, the late 15th century Imperial Villa, and the Synagogue. Further down Via Rossini stands the town's Cattedrale; with remarkable mosaic floor uncovered some ten years ago. If you keep heading straight down Via Rossini you will eventually find yourself on the sea-front and looking at one of the city's most flamboyant buildings, the stunning Villino Ruggeri, one of the finest examples of the Italian Liberty style.
Not a long way from Pesaro is Fano, a charming small seaside resort that doubles as a busy fishing port with an attractive old centre. The Arco di Augusto, erected in 2 AD, is a splendid Roman triumphal arch providing a gateway to the town. The Palazzo del Podestà in the central Piazza XX Settembre is an elegant building now used as venue for concerts and theatrical performances.
A few km inland from Fano is Fossombrone, a picturesque little town hugging the hillside, abounding with antiquities, churches, and elegant patrician residences. Not to be missed: a visit to the Casa Museo Quadreria, a bold work of modern architecture and design featuring a prestigious art collection with paintings by famed 20th century artists.
The beautifully preserved historic center of Urbino is more than worthy of its status as UNESCO World Heritage Site. Over the years the beauty of the city has been increased, by the addition of the meticulously cared for vineyards which now carpet the surrounding hills. Urbino's finest renaissance artworks can be seen in the city's Palazzo Ducale, an imposing 15th century edifice, now seat of the National Gallery of the Marches. Piero della Francesca's "Flagellation of Christ" and "Madonna of Senigallia", and Raphael's "Portrait of Young Woman" are, perhaps, the best-known of the 15th century masterpieces on show.
Proceeding northwards, we will get to the small village of San Leo. Perched on a rocky spur, the town's fortress, now home to a Museum and impressive art collection, is linked to the mysterious figure of Count Cagliostro, the alchemist who claimed to have discovered the elixir of eternal youth and who was sentenced to death by the Inquisition. Cagliostro was imprisoned in the castle of San Leo, where he died in 1795.
In this above described areas there is a number of charming agriturismos or country guesthouses, where you can enjoy genuine local food and wine, such as: Agriturismi Ca’ Serrantonio Ferri in Urbania, Country House Finocchieto or Country House Acquanera, both in Piobbico.