The best Italy city breaks to book in 2024

Looking for a skiing holiday, summer sizzle or glamorous cruise? The Italian landscape is preened for every season on the travel calendar, but none more so than the time-short and culture-hungry traveller’s favourite – the perennial city break.

Famed for its rich regional gastronomy – think bowls of bolognese, wood-fired pizzas and scoops of gelato – Italy’s cities have all the ingredients to tick off sightseeing, culture and history from a city break bucket list.

Tourists may first be drawn to the rustic glamour of the capital, but it’s not just “when in Rome” – the Mediterranean country is a tapestry of ancient ruins, rolling hills and timeless art from boot to heel.

Harbourside island hubs in Sicily in Sardinia blend beach days with Baroque architecture, while Naples and Milan compete to polish the edges of their authentic offerings into holidaymaker-friendly hotspots.

From Renaissance Florence to coastal Cagliari, here are the best cities to visit for the ultimate Italian experience.

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Milan, Lombardy

Once a key player in Italy’s industrial Golden Triangle, Milan has remained a frontrunner in finance and high-end fashion. You’ll notice there’s no shortage of brand names in the dome-topped Galleria Vittorio Emanuele II. However, the northern city is not without old-world charm, from the operas and ballets of Teatro alla Scala to the grand paintings in the Pinacoteca di Brera museum. Not forgetting the ornate Duomo di Milano cathedral with sweeping city views. Even better, all these sights are easily reached via the Campari-coloured tram network.

Where to stay

True to Milan’s industrial roots, nhow Milan is housed in a former electrics factory with a fashionable twist. The hotel brings splashes of orange and purple to its modern, minimalist rooms. It also boasts a a quirky rooftop pool terrace, Turkish bath and Italian bistro in the same style.