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ISSIMO’s Travel Guide to the Milano–Cortina Winter Olympics

December 11, 2025

ISSIMO’s Travel Guide to the Milano–Cortina Winter Olympics

From icy podiums to aperitivo hour, here’s how to do the Winter Olympics the Italian way

On February 6, 2026, Italy hosts the world – quite literally. The Milano–Cortina Winter Olympics officially kick off, unfolding across cities, slopes, valleys, and peaks until February 22 (with the Paralympics following in March). It’s Italy’s third time hosting the Winter Games, but the first with a dual personality: fashion-forward Milan meets the snow-dusted drama of Cortina d’Ampezzo and the Dolomites.

Translation? You don’t have to choose between city culture and mountain adrenaline. This is the Olympics where you can watch figure skating in the afternoon and sip a Negroni by night, or cheer alpine skiers before disappearing into a rifugio for polenta and wine. Here’s how to do it how we would: molto bene.

First Things First: Where the Action Is

The Games open in spectacular fashion at San Siro Stadium, setting the tone with a ceremony that promises scale, wow moments, and a healthy dose of Italian drama.

Milan is your hub for ice sports: figure skating, speed skating, short track, and ice hockey all play out across sleek, newly upgraded venues. It’s the perfect base if you want Olympic energy with museums, shopping, and late dinners built in.

For snow, altitude, and heart-racing descents, the spotlight shifts north. Cortina d'Ampezzo hosts alpine skiing and sliding sports against the jaw-dropping backdrop of the Dolomites, while legendary mountain towns like Bormio and Livigno bring high-speed runs and freestyle flair into play.

The finale? A poetic full-circle moment in Verona, with the closing ceremony staged inside the ancient Arena – because only Italy could end the Olympics in a Roman amphitheatre.

WHERE TO EAT

Milan is full of incredible, stylish places to eat—but some of the most rewarding meals are found in the traditional spots that are a little harder to find if you don’t know where to look. Al Matarel feels like being invited into someone’s dining room: intimate, unmistakably Milanese, and slightly chaotic in the best way. Al Garghet is perfect for long lunches—a true Milan institution that’s traditional, comforting, and unapologetically nostalgic. And then there’s Premiata Trattoria Arlati dal 1936: nothing flashy, just very good food, done the same way it has been for decades.

Getting Around

The good news? Italy has done its homework. Fast trains, expanded metro lines, and Olympic shuttle routes make moving between Milan and the mountains far easier than you might expect, provided you plan a little ahead.

Yes, you can drive, but consider it a scenic option rather than a speedy one. Alpine roads are beautiful, narrow, and weather-dependent, and winter equipment is a must. On competition days, locals will tell you the same thing: leave the car behind, hop on public transport, and arrive relaxed. 

Where to Ski Between Events

Olympics or not, February is prime skiing season, and plenty of slopes remain open if you plan smart.

Cinque Torri

Dramatic rock formations, sunlit runs, and postcard scenery at every turn.

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Lagazuoi

Ride the cable car, ski the legendary descent, stay for lunch with a view.

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Col Gallina

Understated, uncrowded, and wonderfully local, ideal for a slower pace.

Tip: Check daily event restrictions and lift updates – flexibility is key.

Milan Between Medals

When the competition pauses, Milan steps into the spotlight

Catch the Duomo just after opening hours, when the marble still feels hushed

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Lose track of time in Brera, hopping between galleries, bookstores, and cafés

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Follow locals to the Navigli for aperitivo — canals, chatter, Campari in hand

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Plan ahead for The Last Supper — tickets sell out weeks (sometimes months) in advance

Before You Go: ISSIMO-Approved Tips

Dress like an Italian: layers, texture, and one great coat go a long way

Build buffers into your schedule, in case of unexpected (or very Italian) delays

Reserve trains and key dinners early; spontaneity works best once you arrive

Trust local advice, especially in alpine areas: conditions change fast

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