Travel to Italy’s hilltop towns: Fiumefreddo Bruzio, Posada, Castelluccio, Locorotondo, Pitigliano and more
Crumbling castles, houses hewn from caves and spiralling streets — these gravity-defying spots are bellissimi.
‘Impossible” is the response I get over and over again when I ask the Italians I know to choose the best hilltop towns in the country. It’s not that they won’t, they simply can’t. A nation with more than 70 mountain ranges, plus countless smaller peaks and troughs, has a lot of high points. Picking the finest examples is tough.
In this selection we’ve ignored the seven hills of Rome — they’re a story unto themselves — and tried to balance the big-hitters (Matera, Taormina, San Gimignano) with those you might not know: Santa Severina? Pietrapertosa? Brisighella? What they all have in common, though, is a degree of altitude — and an even greater degree of charm.
We’ve travelled from Valle d’Aosta in the north to Sicily in the south. Many date from the Middle Ages and were founded on sites first populated by the Etruscans, who lived from 900BC in what we now call Tuscany and Umbria, as well as parts of Lazio, Emilia-Romagna, Lombardy, Veneto and Campania, until they were “incorporated” into the Roman Empire. These towns and villages are often fortified and topped by castles, with defensive walls and towers, narrow streets and cobbled courtyards, grand palazzi and crumbling ruins, all of which add to that fairytale feel.
Often it seems that time has stood still in these places: in Civita di Bagnoregio it looks as though the inhabitants still live in the 16th century; in La Morra families make wine the way they have for centuries; in Ragusa Ibla, after the 1693 earthquake destroyed the old city the townspeople rebuilt it in the same spot; in San Daniele they have been preserving prosciutto to the same recipe since at least 1453.
What you’ll experience in these places is a very particular sense of atmosphere, a generous welcome, knockout views and a profound respect for history and tradition. And which is my favourite? Oddly, it’s impossible to say.
1. Fiumefreddo Bruzio
Fiumefreddo Bruzio in Calabria takes very seriously its official status as one of the most beautiful villages in Italy. More than 210m up from the beach, the people of this inspirational hilltop community have pulled together to save their medieval home from the fate of so many isolated spots in the south. They have branded themselves a “slow village” with a canteen, ConVivio, showcasing seasonal, regional food (“You eat what is available”). Stay: The Borgodifiume concept offers “a slow journey in a slow village”, including Granatello, an albergo diffuso with five rooms and two apartments split between 17th-century buildings; and a retreat for women with breast cancer at Casa di Rosa. B&B doubles from about $100.
2. Posada, Sardinia
Posada rose from the ashes of a Carthaginian colony on the Tyrrhenian coast to become a stronghold dominated by the Castello della Fava. That got its name when its inhabitants, under fire from the Turks, gave their last broad bean (fava) to a hungry pigeon. The labyrinth of alleyways, steep stairs and tiny piazzas has the air of an Escher print, but seaside panoramas (the beach at San Giovanni di Posada is a highlight) bring you roaring back to this holiday island. Stay: The no-nonsense Hotel Donatella has B&B doubles from about $112.
3. Castelluccio, Umbria
At 1524m above sea level, Castelluccio is the highest and arguably most beautiful village in the Apennines. It was devastated by an earthquake in 2016, but that doesn’t mean you shouldn’t visit, as shops and restaurants still need support and you won’t be disappointed. Castelluccio is backed by snow-capped mountains at the heart of the Monti Sibillini National Park, a complex biosphere perfect for hikers. Go in spring for La Fioritura, when the meadows are a vibrant tapestry of poppies, tulips and cornflowers. Stay: Palazzo Seneca in nearby Norcia has B&B doubles from about $195.
4. Locorotondo, Puglia
This rotund whitewashed ton that hugs the hillside, horizontally, thanks to its circular street plan, as well as vertically. It might have views over the Itria Valley’s patchwork of vineyards, olive groves and conical-roofed trulli huts, but its own architecture of narrow townhouses with gabled roofs is strangely Baltic-looking. It has the prettiest old town centre in the region with an excellent weekly market and remarkably few visitors, which means you’ll always get a table at Trattoria Centro Storico, where Giovanni’s food is second to none. Stay: Leonardi Trulli Resort has rooms in the traditional style; B&B doubles from about $230.
5. Pitigliano, Tuscany
Known as la piccola Gerusalemme, or Little Jerusalem, Pitigliano was, from the 16th century, home to a thriving Jewish community later protected from the Nazis by its neighbours in World War 11. Now a slice of this medieval town is a living museum, the Percorso Ebraico, with an ancient synagogue, plus areas for bathing, baking and wine storage dug from the rock. Try lo sfratto (it means “the eviction”), a baton-shaped pastry conceived by the locals as a grimly humorous reference to sticks used to bang on doors when they were herded into the ghetto. Stay: The homely Dimor’a offers just two rooms; B&B doubles from about $125.
6. Urbino, Le Marche
Urbino is the birthplace of Raffaello Sanzio, one of the superstar painters of the Renaissance. Today, this cultural capital of Le Marche showcases some of the finest art in the region, and not just by Raphael. The grand palazzi hide a wealth of treasures; in the Galleria Nazionale delle Marche, you’ll find works by Titian and Piero della Francesca, while the oratory of San Giovanni Battista has frescoes of the life of John the Baptist by the brothers Salimbeni. Seek out the 200-year-old botanical gardens of Pierina Scaramella, an exotic urban oasis. Stay: Sanpolo 1544, a 16th century-style palazzo, has B&B doubles from about $170.
7. Etroubles, Aosta Valley
Etroubles is reached via a long haul up to the Great St Bernard Pass connecting Italy with Switzerland. This ancient Alpine village looks like a postcard from Heidi, but don’t be deceived. The community is frequented by weekend skiers, summer walkers and art buffs. There’s a permanent museum trail, established by the Fondation Pierre Gianadda in Martigny, and you’ll find sculptures, installations and contemporary paintings by artists including Salvatore Sebaste, Alberto Gambale and Sergio Zanni dotted around. Don’t miss the frescoed sanctuary dedicated to Our Lady of the Snows at Echevennoz, a five-minute drive away. Stay: The chalet-style Hotel Beau Sejour has B&B doubles from about $76.
8. Orvieto, Umbria
The HQ of Cittaslow, the “slow cities” movement, a red-rock Orvieto is a former Etruscan stronghold, sacked by the Romans then reborn in architectural glory in the Middle Ages. Its dramatic position on the edge of a cliff of volcanic tuff, with a sheer drop into the abyss, is eclipsed only by its flamboyant cathedral, a giant that took almost 300 years to complete, with eye-popping frescoes of The Last Judgment within. The Anello della Rupe, a walking trail around the rock, is an excellent way to explore. Stay: The former Benedictine abbey of La Badia di Orvieto, 10 minutes’ drive from town, has B&B doubles from about $193.
9. Vernazza, Liguria
Vernazza is an alternative to the ice-cream-coloured villages of the Cinque Terre that cling to the cliffside above the Ligurian Sea. Each of the five has its high points, but Vernazza, with its tiny harbour, has the added lure of excellent negronis at Ananasso Bar 1985. Such charms come at a price; the 12.8km of trails that link the villages, winding up through a national park and along terraces of olive groves and vineyards, are unbearably crowded in summer, so visit in spring. A Cinque Terre Trekking Card gives walkers access, plus a hop-on, hop-off train pass. Stay: Inntravel’s self-guided walking tour covers stays in three-star hotels; four nights B&B from about $1200 a person.
10. Asolo, Veneto
A 1200-year-old haven of shady porticos, medieval churches, fountain squares and frescoed loggias, Asolo ia backed by the mighty Dolomites. It is so chilled, it’s become a verb: asolare means “to hang out” in colloquial Italian. The poet Giosue Carducci called this “the city of 100 horizons”, best seen from the Strada dell’Architettura trail, with a picnic of prosciutto and pinza fruitcake from Da Ennio. Look for the church of Santa Caterina, with its fading frescoes, and the convent of Sant’Anna, where the travel writer Freya Stark is buried. Stay: Villa Cipriani, once home to Robert Browning, offers touches of old-school style. B&B doubles from about $306.
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