The 2026 Olympic Playbook: Navigating Milan and Cortina Like an Insider

For travelers heading to the 2026 Winter Games in Italy, the sprawling geography is the first challenge. With events spread across nearly 500 miles between Milan, Cortina d’Ampezzo, and smaller Alpine towns, a smooth experience depends on strategy. According to elite travel planners, this isn’t a trip you simply book online.

Milan, hosting the opening ceremony and ice events, is the logical base for many. Top hotels like the Mandarin Oriental and Four Seasons are in high demand, but boutique options like Vico Milano offer privacy. Fulvio De Bonis of Imago Artis Travel, who arranges trips for celebrity clients, suggests the Portrait Milano, a transformed 16th-century seminary. His team secures private access to major sites, from the Duomo’s terraces to Leonardo da Vinci’s 'The Last Supper' at Santa Maria delle Grazie.

In Cortina, the heart of Alpine skiing, logistics tighten. Private transfers from Venice or Milan are key, as local movement relies on shuttles. Accommodations range from the activity-adjacent Hotel de Len to the biking-focused Faloria Mountain SpaResort. For a quieter stay, experts book properties like Ciasa Salares in Alta Badia, famed for its wine cellar.

Dining reveals the true hierarchy of access. While Michelin-starred slopeside lodges like El Camineto draw an international crowd, the real power move is entry to private hospitality suites such as Clubhouse 26. In Milan, the Brera district retains an authentic charm, with Il Solferino as a dinner favorite.

The advice is consistent: navigating these Games requires local expertise. Whether it’s a ski safari with a former champion or a passeggiata down Cortina’s bustling Corso Italia, the best experiences are those arranged behind the scenes.