Winter Olympics fever is in full swing, with the ongoing Milano Cortina 2026 Games shining a bright spotlight on Italy’s mountain regions. If watching wintersport champions like freestyle skier Eileen Gu, who represents China, or Japan’s gold-medal snowboarders Kimura Kira and Kokomo Murase defying gravity against the dramatic snow-capped mountain peaks has you daydreaming about your own Italian alpine escape, consider this your cue to plan your next vacation.
What is often overlooked is that many of Italy’s mountain destinations are not just winter playgrounds, but also suitable as year-round getaways. Ski season can stretch into April, which means there is still time to fit in a winter vacay this season. Or visit in the greener months, when hiking and biking trails open up so you can get your share of forest bathing.
These three Italian mountain regions, all accessible via Milan, each offer a different take on the highland lifestyle.
Holiday at a family friendly hamlet in Sestriere
For a taste of the simple mountain life, head to Sestriere, a ski domain set at 1,600 metres in Italy’s northwestern Piedmont region, roughly a three-hour drive from Milan. Best known for hosting the alpine skiing events during the Torino 2006 Winter Olympics, the area offers well-groomed, competition-grade runs across the vast Via Lattea ski network, which stretches more than 400km across the Italian-French border.
Yet, despite its pedigree, Sestriere is far from intimidating. Beginners and younger skiers will find plenty of accessible pistes and gentle slopes designed for those still finding their snow legs. Several small ski towns dot the region, but for a fuss-free, multi-generational holiday, the chalet-style hamlet of Pragelato makes a practical base. Originally built as an Olympic Village to house athletes, it was later reimagined as a leisure destination and is today home to Club Med Pragelato. Recent renovations have refreshed the resort’s facilities and interiors, preserving its cosy alpine feel while adapting it for contemporary family travel.
The appeal lies in Club Med’s all-inclusive model, which bundles accommodation with ski lessons, equipment rental, lift passes and supervised kids’ clubs for ages two to 17. This removes much of the logistical juggling that often comes with winter holidays, from coordinating lessons to keeping younger travellers happily occupied. Beyond downhill skiing and snowboarding, guests can also try snowshoeing, cross-country skiing and even biathlon, offering a broader introduction to mountain sports.
In summer, Pragelato stands out as one of the few villages in the area that remains open. The focus shifts to warm-weather pursuits such as hiking, cycling and swimming, making the most of long days and clear alpine air.
Seek wellness in the Dolomites
With its iconic craggy peaks, the Dolomites form the beating heart of Italy’s Winter Olympics, with much of the sporting action centred in the towns of Cortina d’Ampezzo, Bormio and Livigno. But for travellers who favour restoration over adrenaline, the town of Brixen, three hours via train from Milan, offers a more contemplative counterpoint.
Set high above the valley and enveloped by spruce, pine and larch forest, the luxury retreat Forestis is designed for switching off. From almost every corner, there are sweeping views of the jagged mountain range, a reminder of just how removed you are from the everyday. The spa is expansive and thoughtfully conceived, with an indoor-outdoor pool, a suite of saunas and a silent room. Therapies incorporate local stones and forest botanicals, grounding the experience firmly in place.
Food is another pillar of wellbeing. The kitchen takes a seasonal, forest-led approach, foraging for herbs and sourcing ingredients from nearby farms. Vegetables are dried or pickled following regional Celtic traditions, bread is baked in-house and jams are preserved on site. For an unforgettable meal, book a private dining meal at forest restaurant Yera, led by chef Roland Lamprecht.
In winter, Forestis offers ski-in, ski-out access to 45km of pistes. A guided snowshoe hike through the Puez-Geisler Nature Park, across frozen streams and untouched snowfields, is particularly meditative. Come summer, hiking and cycling are de rigeuer. For a quieter moment, join a Wyda or Celtic yoga session, which is practiced out in the woods for a deeply grounding finish.
Alpine adventures and thrills at Breuil-Cervinia
Set beneath the unmistakable silhouette of the Matterhorn (known as Cervino on the Italian side of the Alps), Breuil-Cervinia is one of Italy’s most visually striking ski towns. Located in the Aosta Valley and reachable in about three hours by bus transfer from Milan, the resort sits at a lofty 2,050 metres above sea level. Its altitude brings a clear advantage: a long and reliable ski season that typically runs from late October to early May, with the added rarity of summer glacier skiing on the Plateau Rosa.
Downhill skiing is the main draw, with access to wide, confidence boosting pistes as well as more demanding, bucket-list black runs on the slopes of the Matterhorn. Beyond alpine skiing, Cervinia offers close to 30km of cross-country trails, while experienced skiers can venture off-piste on heli-skiing excursions. Other winter pursuits include ice skating, snowmobiling and paragliding, which offers a striking bird’s-eye view of the surrounding peaks.
When the snow melts, Cervinia transforms into an adventure-led summer destination. Via ferrata routes and fixed-rope climbs appeal to those seeking vertical challenges, while downhill mountain biking, hiking and Nordic walking make the most of the open terrain. Golf, horse riding and tennis round out the warmer-weather offerings.
There are plenty of lodges in town, but for a more luxurious stay, Cervino – VRetreats, a Small Luxury Hotel, offers spectacular views of the surrounding mountains.
One final must-do: Cervinia now links directly to Zermatt in Switzerland via the Matterhorn Glacier cable car — the world’s highest alpine cableway crossing. The panoramic views are breathtaking and the novelty of stepping into Switzerland for a day trip makes this a worthwhile side quest.
For more information on Singapore Airlines’ flights to Milan, visit singaporeair.com.
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