Italy’s most stylish city hosts one of the biggest sporting events on the calendar this year: the 2026 Winter Olympics. Milan is sharing hosting duties with Cortina, with the opening ceremony scheduled for the iconic San Siro on February 6. Away from the arenas, Milan’s roster of historic landmarks, stylish streets, and unbeatable dining make it a fixture on any and all travel bucket lists.
Do this: For the first time since 2014, the world’s best ice hockey players will compete for Olympic Gold. The last chance to see Sidney Crosby battling for gold? Get to PalaItalia and Fiera Milano.
Stay here: We love the storied Park Hyatt Milano for a blow-out stay, or B&B Milano Sant’Ambrogio for something more affordable.
📍 Check out our ultimate guide to the Milano Cortina Winter Olympics 2026
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