6 of the best Italian hill towns

1. Brisighella, Emilia-Romagna

Best for: hilltop castles
The region that brought Parma ham and Parmigiano Reggiano to the world has another, lesser-known draw — its hilltop castles. Chief among them is Brisighella’s medieval fortress, which occupies one of three rocky pinnacles looming over the town. The smaller of the castle’s two circular watchtowers contains a tiny archaeological museum, while the walkways between them offer heart-thumping views over the Lamone River Valley, where lines of grapevines meet cypress trees.

Or try: Walled Monteriggioni, which encircles a Tuscan hilltop like a stone crown. It started life as a castle and featured in both Dante’s The Divine Comedy and the video game Assassin’s Creed.

2. Calcata, Lazio

Best for: the arts
A jumble of higgledy-piggledy houses on a rocky outcrop immersed in a sea of green, Calcata looks like a figment of someone’s imagination — fittingly, as the hamlet has been a creative colony since the 1960s. Wander the maze of artists’ studios beneath flower-filled balconies, stopping to browse terracotta ceramics and vintage clothes, and finish up for aperitivo hour in one of the tiny bars on Via Garibaldi. A 20-minute walk away through Parco Valle del Treja woodland is Opera Bosco, an open-air sculpture trail.

Or try: Grotte, near the Valley of the Temples archaeological site in Sicily, which has been revitalised by street art, with murals alongside the caves that gave the town its name.

3. Barolo, Piedmont

Best for: wine-lovers
Home to Italy’s most celebrated red, tiny Barolo presides over the terraced vines of the Langhe Hills. A UNESCO-protected area, this region grows Piedmont’s signature nebbiolo grape, thought to be named after the fog that sometimes cloaks the undulating hills around harvest time. Barolo itself is the picture of rustic charm, its ochre buildings taking on vivid shades of peach melba when cast in the sunset’s amber glow. Housed in the town’s medieval castle, interactive exhibit WiMu explores the town’s long history of viticulture.

Or try: Montalcino, surrounded by Tuscan vineyards, where ancient walls encircle redbrick buildings and seemingly endless enoteche (wine shops).

4. Urbino, Marche

Best for: Renaissance splendour
In the 15th century, this hilltop outpost rivalled Florence as a cultural centre. Today, it receives far fewer visitors than its cousin to the west. Signs still point to its former life, with Palazzo Ducale the most prominent among its jumble of honey-hued buildings. Now home to the Galleria Nazionale delle Marche, it houses works by Titian and Marche native Raphael, in suitably grand surrounds. The town’s sizeable student population saves it from becoming a living museum, filling the streets with life during term time.

Or try: Clifftop Pitigliano is carved into volcanic rock, and its striking medieval and Renaissance skyline overlooks the gorges of the Tuscan Maremma region.

5. Tivoli, Lazio

Best for: ancient history
On an outcrop of the Sabine Hills, Tivoli was once a summer retreat for the Romans, and its two UNESCO sites remain monuments to the empire’s power and privilege. Villa Adriana, with its rock arches flanking emerald pools, once belonged to Emperor Hadrian; 16th-century Villa d’Este has a landscaped garden, with rows of cypresses standing sentry beside spraying fountains. In town, locals shade themselves in the squares beneath white parasols, flanked by buildings coloured raspberry pink and lemon yellow.

Or try: The small Umbrian city of Orvieto, which overlooks vineyards and olive groves from its plinth of rock. It’s home to one of Italy’s most beautiful gothic cathedrals.

6. Pietrapertosa, Basilicata

Best for: clifftop drama
The savage beauty of the Lucanian Dolomites backdrops Pietrapertosa, a small, terracotta-roofed town that’s a worthy rival to more famous Matera, 50 miles east. Sat within a natural amphitheatre, its main event is the Angel’s Flight: a high-flying zip-wire that propels participants to the neighbouring town of Castelmezzano at speeds of up to 75mph. Recover afterwards with homemade pasta at Le Rocce. The restaurant’s speciality is maccheroni mollicati (macaroni and breadcrumbs) with local Crusco peppers.

Or try: Civita di Bagnoregio — the ‘dying town’ north of Rome, nicknamed for its precarious clifftop perch. To reach it, climb a steep, 1,200ft-long footbridge.