Bypassed in favour of the headline towns such as Positano and
Amalfi, Atrani is the Amalfi Coast’s best-kept secret. Nestled
between two cliffs, it’s the smallest hamlet in
southern Italy and one where, along steep alleys and peeling
paintwork, you can sink into the laid-back vibe. Sorbet-hued
dwellings cluster around the medieval piazza, from where a
passageway leads to the Tyrrhenian Sea. Attractions include the
10th-century Church of San Salvatore de’ Birecto and the Grotto of
the Saints, a natural cave decorated with Byzantine frescoes.

With a population hovering around 800, this cliffside village
ringed by the Lucanian Dolomites
is among the most otherworldly places you’ve never heard of. Enter
via a tunnel carved into the rock to explore narrow streets, sample
local, farm-fresh food and knock back regional wines in family-run
trattorie. Visit Pietrapertosa on the opposite side of the valley
to take the Volo dell’Angelo – “Flight of the Angel” – zipwire back
to Castelmezzano.

Once connected to surrounding towns by road, Civita di
Bagnoregio is today accessible by a solitary footbridge thanks to
2,500 years of land erosion and earthquakes. Nicknamed “la città
che muore” – the dying city – and with a population that doesn’t
reach double figures, the town rises from the mists as if in a
fairy tale. Wander the Renaissance palazzi and explore the
3,000-year-old Etruscan caves, one of which serves as a chapel.

An hour’s drive from Bari, this Unesco World Heritage Site is
famed for its 1,500 trulli. These whitewashed, conical-roofed
buildings date from the 1500s when the ruling Acquaviva family
ordered locals to build their homes without mortar – in the event
of a royal inspection, structures could be taken down and they
could avoid paying royal taxes. Today, the trulli serve mainly as
souvenir shops, restaurants and accommodation for visitors. Head to
the Piazza del Popolo, where the Belvedere Trulli offers
spectacular views across the town.

A patchwork of sun-bleached buildings,
Procida‘s oldest fishing village is a haven of south Italian
charm – Il Postino and The Talented Mr Ripley were filmed here.
Wooden boats line the 17th-century Marina Corricella, which buzzes
with fishermen and vendors. Grab a table on the waterfront for an
Aperol spritz and Corricella’s signature plate of sea urchin
spaghetti. The Fortress Terra Murata, a former prison, offers great
views over the Gulf of Naples.

A rainbow of houses hugging the rugged Ligurian coast, this
ancient borgo is the oldest and most romantic of the five hamlets
that comprise the Cinque Terre. Enclosed by steep terraces, lemon
groves and vineyards, it’s best reached by foot, via the scenic
Lovers’ Lane which connects to neighbouring Riomaggiore. Meander
the warren of alleys which climb to medieval watchtowers before
kicking back with a glass of sweet Sciacchetrà wine.

Just 20km from Siena, this
fortified citadel makes visitors feel as if stepping into a bygone
medieval era. Encircled by 13th-century walls, Monteriggioni
started its life as a castle – Dante compared its 14 imposing
watchtowers to “horrific giants” in his Divine Comedy. Enter
through the Porta Franca gate and visit the Romanesque Church of
Santa Maria Assunta or the Armoury Museum. Nearby Borgo Stomennano
is a 17th-century hamlet-turned-hotel with vistas across Chianti’s
vineyard-strewn landscapes.

Some 5,000ft above sea level, Castellucio is the highest village
in the Apennine Mountain Range – and arguably the most charming
too. Located in Monti Sibillini National Park, its lush, fertile
plains backdropped by dramatic snow-dusted mountains are ideal for
trekking. Visit in spring during La Fioritura – The Flowering –
when blooming poppies, violets and rapeseed decorate the
valley.

Lake Orta is known among the Milanese as La Cenerentola –
Cinderella – so much is it considered the discreetly superior
sister to the more
showy lakes of Como and Maggiore. Jutting out from its eastern
bank, Orta San Giulio is unspoiled by tourism and a favourite
destination among writers such as Nietzsche, Byron and Carol Ann
Duffy. Follow a tangle of narrow streets to the lakeside Piazza
Motta, where village life plays out among faded ochre buildings, or
visit Sacro Monte, a Unesco-protected site of religious
pilgrimage.

On the southern side of the Monte Argentario peninsula, Porto
Ercole is a popular staycation spot for wealthy Romans and the site
where, in 1610, baroque painter Caravaggio died of malaria. Stroll
the network of narrow streets or worship the sun like an Italian
along the sandy Feniglia beach or in one of many natural coves.
Once frequented by the likes of Jackie Kennedy, Slim Aarons and
Sophia Loren, Il Pellicano is among the area’s
stand-out hotels, with timeless charm, sublime food and unending
coastal views.

An hour’s drive from mainland Venice, this charming small town
of Renaissance-era buildings, palazzi and Romanesque churches is
backdropped by the peaks of Gusela del Vescovà, Mount Serva and
Monte Talvena. Perched above the Piave River, it’s the perfect
launchpad for exploring the surrounding mountains. Fuel up for
hikes with noteworthy Italian cheeses: flaky Malga Bellunese and
Schiz, a semi-soft cheese often served fried in butter.

Val Badia is among the most enchanting pockets of the Dolomites;
its mythical landscapes inspired the fantasies of JRR Tolkien.
Here, the comune of Badia is so far north that it’s a far cry from
what most would expect from an Italian village – most residents
speak either the local dialect of Ladin or German. In winter the
surrounding massifs make this a hotspot for skiers; come summer
cyclists zip through the town en route to Passo Valparola.