Milan City Breaks & Holidays 2025/2026 from £189pp

Why go to Milan

Fall for Italy’s second city, and you’ll fall for good. Dig below the suave surface, and holidays in Milan are richly rewarding.

The F words

Milan excels at many things, but, above all, it excels at fashion. The city hosts numerous events and trade fairs, is inhabited by often dauntingly dapper locals, and boasts boutiques by everyone from Armani to Zegna.

There’s also serious financial oomph: as well as being home to a battalion of bankers, Italy's stock exchange is located here.

The industrial powerhouse scores too for football (calcio) – multi-European champions AC Milan and Inter Milan share its legendary San Siro stadium – and food, with a raft of newly Michelin-starred chefs making it one of 2025’s culinary must-visit destinations.

Underrated wonders

Milan also has a reputation for being reserved, a stereotype that’s based upon the city’s often grey, modern buildings and business-like locals. Give a holiday in Milan a chance, however, and you’ll encounter culture, charm, flamboyance and beauty.

There’s La Scala, a world-leading opera house, the Pirelli tower, a triumph of 1960s modernism, and grand Gothic cathedral Il Duomo, one of the world’s finest buildings.

And then there’s the Santa Maria alle Grazie Basilica, home to Leonardo da Vinci's mural ‘The Last Supper’. Art doesn’t come any more vital than this masterpiece.

Secrets and highs

This is also a place where incredible galleries hide in plain sight and where fantastic cocktail bars are squirreled away in unpromising courtyards: a place that rewards exploration and enterprise.

Stroll districts such as the canal-filled Navigli or raffish Corso Como and you’ll encounter Milan’s own dolce vita (good life).

Here, gelaterias, aperitivibars and cheap pizzerias accompany high-design furniture stores and impressive, plant-swathed high rises.

La posizione perfetta

Another plus of cheap city breaks in Milan is the dreamy location. Lake Como and ski slopes are both within reach as a day-trip, as are vineyards, beaches and all-inclusive resort hotels.

When to go to Milan

Spring and autumn are perfect for holidays in Milan: the weather’s warm and the city fizzes with fervour. Hotel rooms can be difficult to find and prices soar during the various fashion and design shows, so book well in advance.

Winter climes sometimes dip below 0C (32F), although pretty windows and fairy lights make the Christmas period magical and ideal for a short Milan city break.

Humid summers see many shops close in August as everyone takes long vacations.

Milan city breaks are cheapest in winter, Christmas aside, and in August when holiday package deals are common.

If you’re coming for a long Milan weekend in 2025, beware that many museums shut on Mondays.

What to do in Milan

Events for your diary

The pre-eminent fashion show is Milano Moda Donna, with invitation-only catwalk shows taking place around the city. ‘Autumn-Winter’ takes place in February, and ‘Spring-Summer’ in September.

Involving a half marathon and a shorter (15-kilometre/9.3-mile) race, Stramilano effectively shuts central Milan for a weekend in March. Corso Sempione is the best viewpoint.