This harmonious piazza has been Ascoli's salotto (drawing room) since Roman times. The elegant rectangular space is flanked by the Chiesa di San Francesco and, on the west, the 13th-century Palazzo dei Capitani del Popolo. The 'Captain's Palace' served as the seat of the city's Pontifical Governors for centuries and...

　　This monumental church, its southern flank edging onto Piazza del Popolo, is named after St Francis, who is said to have visited Ascoli in 1215. It was consecrated in 1371, but construction, which started in 1258, took some 300 years and it wasn't until 1549 that the church was completed....

　　One of Venice's most photographed sights, the Bridge of Sighs connects Palazzo Ducale to the 16th-century Priggione Nove (New Prisons). Its improbable popularity is due to British libertine Lord Byron (1788–1824), who mentioned it in one of his long narrative poems Childe Harold's Pilgrimage. Condemned prisoners were said to sigh...

　　Ascoli's archaeological museum holds a small collection of artefacts from the Piceni and other European peoples dating back to the first centuries AD, as well as a fantastic mosaic floor featuring a stunning centrepiece: a dual-sided depiction of an old/young Roman god Janus (an optical illusion depending on your viewpoint)....

　　This 40m-high tower is closed to the public but is the tallest of the town's medieval towers. Abutting it is the Palazzetto Longobardo, a 12th-century Lombard-Romanesque defensive position that is now home to the Ostello dei Longobardi youth hostel, while just to the north is the well-preserved Ponte Romano, a...

　　The Museo dell'Arte Ceramica traces the development of ceramic production in Ascoli and displays works from Italy's famous pottery towns, including Deruta, Faenza and Genoa. Don't miss Francesco and Carlo Grue's 18th-century framed pictorials, a sort of Old World comic strip. ...

　　This enchanting albergo diffuso, with 28 distinctive rooms and suites scattered throughout the village, was what helped rescue Santo Stefano from oblivion. Designed to reignite Italy's lesser-known settlements without scrimping on luxury, they marry traditional handmade bedspreads and rustic furniture with under-floor heating, mood lighting and divinely deep bathtubs. Everything...

　　Topped by a pair of mismatched towers, Ascoli's cathedral was built in the 16th century and dedicated to St Emidio, the city's patron saint. Its most prized possession is the three-section Polittico di Sant'Emidio (Polyptych of Saint Emidio; 1473) by the Venetian painter Carlo Crivelli in the Cappella del Sacramento....

　　Set around a tree-shaded courtyard, the second-largest art gallery in Le Marche sits inside the 17th-century Palazzo Comunale. The palace's aristocratic halls are lined with outstanding works of art and sculpture by major Italian artists such as Titian, Carlo Crivelli and Guido Reni, as well as a collection of religious...

　　The 14th-century Chiesa di San Pietro Martire is dedicated to St Peter of Verona, the 13th-century saint who founded the Dominican community at Ascoli. The solemn Gothic church houses the Reliquario della Santa Spina, a gilded silver reliquary containing what is said to be a thorn from Christ’s crown. ...