Outside of summer, February is an obvious time to go to Venice,
with Carnevale in full swing, parades lining the canals and
bridges. It’s also rammed with tourists, though. To see La
Serenissima living up to her serene moniker, January is worth a
try. There’s also the city’s inaugural Cocktail Week, 13-19
December, when top bars and mixologists will open their doors for
masterclasses and special events. If you’re lucky, you’ll get
impossibly beautiful misty mornings over the Grand Canal, followed
by crisp afternoons with blue skies.

Stay:
Splendid Venice

The region of Veneto is most famously known as being home to
Venice and Verona, but venture further out and you’ll discover an
incredible nature oasis with beautiful lakes and mountains. The
surrounding region of Padua is home to popular termes (thermal
spas) such as Abano and Montegrotto, where pampering dips have been
a much-loved winter tradition for Italians since pre-Roman times.
The natural thermal waters at Montegrotto reach up to 37 degrees
Celsius, and are said to have a multitude of healing powers.

Stay: Ariston Molino
Buja

The Eternal City also happens to be evergreen in its appeal. In
fact, as anyone who’s spent a sweaty August afternoon queuing for
the Colosseum can attest, occasional rain and snow is far
preferable. On 6 January, festive celebrations start all over again
for Epiphany, when La Befana brings gifts to children and bakeries
such as Roscioli are filled with seasonal treats. Sightseeing is
far quicker without the crowds, leaving more time to stroll around
local neighbourhoods such as the Jewish Ghetto (where Beppe e i
suoi Formaggi makes a great lunch spot) or the colourful markets of
Trastevere.

Stay: Mama Shelter, Rome

This Umbrian city is known for its annual chocolate festival,
usually held in October, which draws in around a million visitors
each year. Enjoy experimental chocolate tastings, workshops, and
artisan markets within the cobbled city centre. There are even
chocolate-themed spa days and climbing walls, run by Italy’s
best-known chocolate brand, Perugina. Sound too sickly? The ancient
city is also steeped in Etruscan, Roman and medieval history, being
home to one of Europe’s oldest universities, a jazz festival and
engaging theatre season throughout the winter months.

Stay: Borgo Bastia Creti

The Renaissance city finally comes up for air from endless tour
groups once summer is over, with roasted chestnuts sold by vendors
around Piazza della Repubblica, vin brulé (mulled wine) and other
seasonal treats such as castagnaccio (chestnut, pine and rosemary
cake) filling bakery windows and tempting Florentines into the city
centre. It also happens to be truffle season. Stock up on the good
stuff at Truffle
Italia or head out into the hills to try foraging for your own.
In March, La Festa delle Donne is celebrated on International
Women’s Day, which sees the city filled with fragrant yellow mimosa
flowers.

Stay:
Bernini Palace Hotel

While coastal hotspots such as Taormina and Siracusa largely
shut up shop outside of peak season, the wild interiors of Sicily
are a fascinating place to visit in the winter months. This being
citrus season, piles of blood oranges and fragrant lemons fill
market stalls across the island. One worthwhile destination deep in
the countryside is Anna Tasca Lanza – a hub for Italy’s Slow Food
movement, where visitors can take part in an immersive two-month
Cook the Farm course from January to March each year. The
19th-century farmhouse in which it’s held is a wildly uncommercial
homage to Sicilian ingredients and cooking: expect freshly churned
ricotta for breakfast, ripe, sun-dried tomatoes, handmade Sicilian
cannoli and blood-red mulberries from the garden. Accommodation is
available at Case Vecchie, the collection of crumbling farm
cottages. Shorter courses are also available, teaching you how to
cook and eat your way through the island’s food heritage.

Stay: Anna Tasca Lanza

Home to more than just Romeo and Juliet, the most romantic of
Italian cities is a prime spot for off-season long weekenders. The
historic centre is pretty and compact. Steeped in culture, it
offers a rich winter season of opera and theatre. The seven bridges
across the Adige make for enchanting winter strolls, punctuated by
hot chocolates and sugary fritole – traditional deep-fried
fritters. If you’re there for longer, volunteer with The Juliet
Club, a quaint institution that sees an army of letter-writers
sending love advice to heartbroken correspondents from across the
globe.

Stay: Cinque

A somewhat forgotten region near Lake Garda in the north of
Italy, Trentino has it all: award-winning locally produced wines,
active adventure, wellness, peace and spellbinding scenery. The
city of Trento is magical around Christmas, fusing German and
Italian traditions in the charming festive market against the
backdrop of the Piazza Duomo. On rainy days, peruse the medieval
frescoes of Buonconsiglio Castle or explore the many gastronomic
delights the city has to offer.

Stay: Locanda in Borgo