Milan’s Olympic Moment – Highlights a Majestic Winter Playground
Milan has always understood the art of being watched. This is the city of runway reveals and opera openings, of aperitivo hour conducted like a ritual, of discreet doors that open into rooms where everything is just a little more polished, a little more intentional. Now, with the Olympics drawing the world’s attention north, Milan becomes something else too: a gateway. Not just to sport, but to a sweep of landscapes—Dolomite peaks, Lombardy valleys, Trentino forests—where winter is at its most cinematic.
The magic of a Milan vacation during the Games isn’t simply “seeing events.” It’s the feeling of waking up in a design hotel to the soft hush of a city dressed for the world stage, spending late morning among Duomo spires and boutique galleries, and then slipping out toward the mountains like you’ve been handed a backstage pass to the Alps. Milan is your base of operations—effortless, elegant, connected—while the venues are your excuses to explore places you might never have prioritized otherwise.
Below is the guide to the Olympic venues, not just a list of events but rather a blueprint for a perfect Italian vacation, not just a calendar item.
Ski Venue | Ski Resort / Town | Region | Olympic Events |
| Tofane Alpine Skiing Centre | Cortina d’Ampezzo | Veneto | Women’s Alpine Skiing |
| Stelvio Ski Centre | Bormio | Lombardy | Men’s Alpine Skiing, Ski Mountaineering |
| Livigno Snow Park | Livigno | Lombardy | Snowboarding, Freestyle Skiing |
| Livigno Aerials & Moguls Park | Livigno | Lombardy | Aerials & Moguls (Freestyle) |
| Predazzo Ski Jumping Stadium | Predazzo | Trentino | Ski Jumping, Nordic Combined |
| Tesero Cross-Country Skiing Stadium | Tesero (Val di Fiemme) | Trentino | Cross-Country, Nordic Combined |
The Milan Effect: Why is Milan a Perfect Italian Vacation Destination?
There’s something uniquely satisfying about pairing Milan’s urban glamour with the raw beauty of the Alps. One moment you’re under the glow of Brera’s street lamps with a cashmere scarf at your collar; the next, you’re looking at snow that seems to have been airbrushed onto a mountainside.
Luxury travel isn’t only about upgrades—it’s about transitions that feel seamless. Milan delivers that. It’s a city built on refined movement: private transfers that feel like gliding, high-speed rail that removes friction, day plans that flow from espresso to art to aperitivo without a single clumsy pause. Even after the Olympics spotlight fades, Milan remains that elegant hinge between city indulgence and Alpine wonderland.
The venues become anchor points, and everything else becomes story: the hotel breakfast that lasts longer than you intended; the boutique you duck into “just to browse” and leave with something tailored; the mountain lunch that turns into a two-hour experience; the final glass of Barolo back in Milan as the city hums with international energy.
What makes Cortina d’Ampezzo A Great Destination for an Italian Getaway?
If the Olympics are a spotlight, Cortina is made for it. This is Veneto’s jewel of the Dolomites—an alpine town that doesn’t try too hard, because it never had to. Cortina’s luxury is the kind that looks natural: wooden balconies, fur throws, fireside lounges, the sense that winter here is a tradition rather than a season.
Tofane Alpine Skiing Centre brings the precision and power of Women’s Alpine Skiing to a backdrop that feels like a film set. Even if you don’t ski, Cortina invites you to participate in mountain life the way Italians do: slowly, stylishly, and always with a good lunch involved.
How to travel to Cortina from Milan?
- Consider Milan as the start of a two-part trip: a few nights in the city for culture and shopping, then a transfer into Cortina where the pace turns romantic and alpine.
- Treat the journey as part of the experience—chauffeured comfort, scenic views, and an arrival that feels like stepping into a postcard.
What makes it irresistible beyond the event:
- Après in Cortina is a mood: hot chocolate that’s actually decadent, wine bars that feel intimate, restaurants where you taste the Alps through an Italian lens.
- The Dolomites aren’t just mountains—they’re sculptural. When the light hits them, everything feels heightened, like nature decided to dress up too.
Bormio and the Stelvio Ski Centre: Speed, Heritage, and Lombardy’s Mountain Soul
Lombardy’s alpine side is different—less “see and be seen,” more “discover and fall in love.” Bormio is the kind of place that rewards travelers who want authenticity with a polished edge. It’s historic, atmospheric, and famously tied to wellness—making it an ideal complement to Olympic intensity.
Stelvio Ski Centre hosts Men’s Alpine Skiing plus Ski Mountaineering, a combination that feels like an invitation to experience the Alps in two moods: thrilling spectacle and rugged endurance. Bormio’s real ace, though, is how it lets you balance adrenaline with restoration.
This is where you travel like an insider:
- Watch the speed events, then pivot into a thermal spa afternoon that resets your entire nervous system.
- Schedule dinners that feel cozy but elevated—local flavors, excellent wine, and the comfort of a place that isn’t performing for tourists.
Why Bormio is a luxury traveler’s secret weapon:
- The mountains here feel closer, more intimate—less like scenery, more like a presence.
- The “luxury” is in the contrast: crisp air, stone streets, and then warmth—steam rising, a robe waiting, a glass poured.
Livigno: The Alpine Playground for Freestyle, Snowboarding, and Pure Winter Joy
If Cortina is elegance and Bormio is heritage, Livigno is energy—bright, sporty, and unapologetically fun. It’s also where the Olympic program leans playful: Snowboarding, Freestyle Skiing, and Aerials & Moguls bring a different kind of glamour. Think less tuxedo, more performance—athletes who feel like artists in motion.
Livigno has two focal points:
- Livigno Snow Park (Snowboarding, Freestyle Skiing)
- Livigno Aerials & Moguls Park (Aerials & Moguls)
Even as a spectator, you’ll feel it: the crowd reacting in waves, the music, the visual impact of tricks against a white sky. It’s the kind of Olympic experience that makes you want to do something afterward—ski a run, try something new, laugh more than you expected.
How to turn Livigno into a luxury escape:
- Make it a stylish alpine “play week”: mornings on the slopes (or at least on scenic terraces), afternoons in boutiques and cafés, evenings that feel celebratory.
- Build in one big indulgence a day: a tasting menu, a wellness session, a private lesson, a snowmobile experience (if that’s your speed). Luxury isn’t only quiet—it can be exhilarating too.
Why it inspires travel beyond the Games:
- You’ll leave with a new version of winter in your mind: not cold and grey, but bright and alive.
- Livigno gives you permission to be playful—without sacrificing comfort.
Why is Trentino a Great Skiing Destination in Italy?
Trentino brings a different kind of luxury—the kind that feels clean, pine-scented, and quietly premium. The landscapes are storybook, and the Nordic events are mesmerizing in a way that surprises people who assumed they’d only care about downhill skiing.
Here, two venues frame your experience:
- Predazzo Ski Jumping Stadium (Ski Jumping, Nordic Combined)
- Tesero Cross-Country Skiing Stadium in Tesero (Val di Fiemme) (Cross-Country, Nordic Combined)
Ski jumping is pure theater—silence, anticipation, flight. Cross-country is endurance and elegance, a slow burn of athletic excellence that feels almost meditative to watch. Val di Fiemme, meanwhile, is the kind of region that makes you want to linger: forest walks, cozy restaurants, refined mountain hotels that focus on wellness, food, and the craft of relaxation.
A Milan-First Luxury Rhythm: How to Make the Whole Trip Feel Effortless
To keep the experience distinctly “Milan vacation” rather than “sports trip,” think in layers:
Layer 1: Milan indulgence
- Mornings in the city: espresso, art, architecture, shopping.
- Evenings: aperitivo culture, fine dining, and the kind of hotel bar where you actually want a nightcap.
Layer 2: Alpine chapters
- Pick one venue region as your primary mountain base (Cortina, Bormio, Livigno, or Val di Fiemme).
- Add a second region as a contrasting mini-escape if time allows.
Layer 3: The memory-makers
- Private transfers, upgraded rail, concierge planning—whatever removes friction and adds ease.
- One “signature experience” per region: spa rituals in Bormio, Dolomite views in Cortina, playful slopes in Livigno, forest calm in Trentino.
Because that’s the real inspiration here: the Olympics don’t just put Milan on the map (it’s never needed help). They give you a reason to travel outward—to see Northern Italy as a set of interconnected worlds, each with its own flavor luxury.
And when you return to Milan after the mountains—cheeks a little pink from alpine air, boots swapped back for something sleek—you’ll feel it: you didn’t just attend an event. You followed a thread from city glamour into the snow, and you let it pull you into places that deserve far more than a passing glance.
That’s the kind of trip you remember. The kind you start planning to repeat—long after the Olympic flame has moved on.
Milan Vacation FAQ's
What’s the most luxurious mountain destination in Italy?
Cortina d’Ampezzo is widely associated with classic alpine glamour—designer boutiques, upscale hotels, refined après, and dramatic Dolomite scenery that feels tailor-made for a luxury escape.
Should I stay in Milan the whole time or split my trip between Milan and the mountains?
For a luxury feel, split the trip. Milan is perfect for the “city chapter,” but staying a few nights in the mountains is what delivers that immersive, cinematic experience
Why should I take a vacation to Milan and the Dolomites?
Absolutely. The Olympic venues highlight some of Northern Italy’s most beautiful regions—Dolomites (Cortina), Lombardy Alps (Bormio/Livigno), and Trentino (Val di Fiemme). The Olympics simply give you a “reason to go” and a special atmosphere while you’re there.
What’s the best Italian spot for scenic photos and “wow” landscapes?
Cortina d’Ampezzo is the standout for iconic scenery. The Dolomites are visually dramatic in a way that feels almost unreal—especially at sunrise and late afternoon when the light turns the peaks warmer and softer.
What’s the best Italian Destination for wellness and relaxation?
Bormio is ideal for wellness-focused travelers thanks to its strong spa culture and restorative vibe—perfect if you want to balance Olympic excitement with deep relaxation.