From urban culture to snowy slopes: this Northern Italy itinerary has it all

If you love active winter holidays, set your sights on Milan and the towering mountain ranges to the city’s north, where you’ll find ski resorts and winter sports aplenty. With a ski season that runs until early April, Northern Italy buzzes with world‑class sports and culture, stunning snowy landscapes and a magical atmosphere.

Plan an itinerary that takes in both city and mountain to pair the sophisticated energy of the country’s fashion capital with dramatic alpine vistas. It’s the ideal mix of urban excitement and rural adventure, experienced in a single trip.

Whether you’re planning to hit the slopes, explore the region’s winter trails or indulge in the glorious cuisine and hospitality on offer, here’s our guide to an unforgettable Italian winter escape.

Cultural activities in Milan

Sports and culture fans have plenty in store in Milan, a city that rewards curiosity. San Siro Stadium, home to Inter and AC Milan, beckons football fans, whether for a match or behind-the-scenes tour. And, of course, Da Vinci’s The Last Supper painting at Santa Maria delle Grazie remains a must-see (advance booking required). An early-morning walk through Piazza del Duomo offers a crowd-free view of the city’s Gothic cathedral, while the Brera and Navigli neighbourhoods provide a snapshot of everyday Milanese life.

Where to go skiing from Milan

A few hours’ train or car journey from Milan, the Dolomites offer a varied winter sports landscape, supported by well‑known centres. The town of Cortina d’Ampezzo is home to the expansive Cortina d’Ampezzo Ski Resort, part of the Dolomiti Superski network, connected by one lift pass and offering 120km of slopes, with terrain suitable for beginners through to expert skiers and snowboarders.

Col Gallina, Cinque Torri and Lagazuoi all offer panoramic runs and gentler pistes, with typically excellent conditions.

In the Italian Alps to the west, not far from spa town Bormio, Santa Caterina Valfurva is celebrated for technical downhill slopes, and Cima Piazzi – San Colombano for treelined trails. Near the Swiss border, Aprica offers easy-going pistes ideal for cruising, while farther along the valley, family-friendly Passo del Tonale rises towards the Presena Glacier.

Where to stay in Northern Italy

A break during the colder months is your chance to hole up and really feel at home in one of Milan’s stylish hotels. Seeking understated luxury? Try The Carlton or Portrait Milano – both located in the Fashion Quadrangle. The former impresses with tastefully designed interiors; the latter occupies a former seminary, reimagined with a fashion-focused approach.

In Cortina, Ancora Cortina, newly reopened after a renovation led by Diesel founder Renzo Rosso, blends mountain charm with modern luxury. Meanwhile, Hotel de Len offers a contemporary take on the traditional chalet, with clean lines and a strong sustainability ethos.

Not far away, in San Cassiano, sits the recently opened Aman Rosa Alpina, a gorgeous new mountain retreat perfectly placed for exploring the region’s scenery, complete with interconnected suites for multi-generational stays. It joins an ultra-luxurious Dolomites hospitality scene that includes Como Alpina Dolomites, an architectural marvel providing chic lodge-style accommodation on the slopes of the Alpe di Siusi ski area.

Where to eat in Milan and the Dolomites

Winter sports and alpine landscapes demand hearty classics and comfort food. In Milan, both await at Al Garghet , a beloved spot serving homestyle dishes in rustic, unfussy surroundings. Trattoria del Ciumbia offers similar fare – cassoeula (cabbage and pork stew), mondeghili (fried meatballs) and ossobuco (veal shanks) with saffron risotto – but in a sleeker space.

In Cortina, Al Camin serves regional dishes with a contemporary twist, while the one-Michelin-starred Ristorante Tivoli is famed for its refined take on Dolomites cooking. Farther afield, high-altitude rifugi (mountain lodges) are destinations in their own right: Maso Runch-Hof offers comforting Tyrolean fare in a wood-panelled setting near the Puez-Geisler Nature Reserve, while Rifugio Col Alt affords sweeping Dolomites views.

Where to buy winter gear in Italy

Naturally, a sporty holiday in Northern Italy calls for serious winter gear. Italian outdoor brands Moncler, Colmar, La Sportiva and Salewa all have flagship shops across Milan and are prized for quality as much as style.

Cortina carries many of the same labels, yet the town is also ideal for sourcing locally made souvenirs and artisanal goods. La Cooperativa di Cortina is a one-stop shop for regional products and gifts, while Boarderline Cortina rents ski gear, allowing you to travel light.

How to get around Northern Italy

Significant upgrades have been made to transport and infrastructure across the region in recent years. Dedicated shuttles now link Milan with alpine towns, offering a stress-free alternative to driving. Milan’s public transport has also expanded, with new electric metro trains and additional rail connections.

Driving is possible, with rentals available at Milan’s airports and main railway station, but winter tyres or snow chains are mandatory in many alpine areas from mid-November to mid-April. Roads can be narrow, icy and congested during winter months, so allow extra time for mountain passes and parking.

A Milan local’s top tips

1. Pack warm layers and sunscreen.

2. Prepare for busy town and city centres.

3. Book transport early where possible.

4. Download apps ahead of time due to variable Alpine internet coverage.

5. Bring cash, though credit cards are widely accepted.

6. Watch out for fast-changing weather conditions.