How to Avoid a Travel Flop During the Milan Winter Olympics

Italy done right starts in our belly

Next week, the Milano Cortina 2026 Winter Olympic Games arrive in Milan and, once again, Italy will do what it does best: look effortlessly good. Mountains, historic cities, impeccable food, and people who somehow pull off scarves at all times of day. On paper, it’s impossible to go wrong.

And yet, it happens. Quite often.

If this sounds familiar, blame the same logic that sank the recent romcom Under the Stars, showing these days on Prime. The film had everything it needed. Attractive leads, a sun-soaked Italian setting, a classic love-story arc and respected actors in supporting roles. And yet, it still managed to feel strangely flat, like a perfectly styled dish that never quite developed any flavour.

Italy wasn’t the problem. The approach was.

One thing the film actually got right is the setting of its main accommodation. The place where the characters stay, run by the protagonist’s father, functions much like a small bed and breakfast. Meals are central, people sit together, and food becomes the reason strangers talk, linger and exchange stories. As an idea, it’s genuinely strong. The problem is that the film never quite knows what to do with it, beyond using it as a convenient backdrop.

Which is a shame, because that instinct is exactly where real Italian magic tends to happen. As The Guardian pointed out, the film’s characters often feel like the result of an AI prompt for “attractive romantic comedy protagonists”. Italy, too, is treated in a similar way, more as a concept than a place. Beautiful, yes. Convincing, not really.

This is how travel to Italy can go wrong, particularly during global events like the Olympics. When a country becomes scenery rather than a participant, it’s easy to collect images without collecting memories. You see everything and somehow feel very little.

Italy already has every landscape that appears on lists of the world’s most romantic places. Coastlines, countryside, alpine villages, piazzas washed in golden light. None of this is in short supply. What is often missing is contact.

Milan, in particular, suffers from this misunderstanding. Known for fashion, finance and efficiency, it can appear polished to the point of emotional distance. During the Olympics, when the city is operating at full spectacle, that impression will only grow stronger.

But Milan isn’t meant to be experienced at scale. It’s meant to be entered quietly, preferably through someone’s front door.

The simplest way to do Italy properly is also the most Italian solution imaginable: start with a table. Not a fancy restaurant res made months in advance, but a table inside a home. Let’s face it, Italy does food well. You do not need Michelin-starred restaurants to prove that to you. One where the food comes with stories and the conversation isn’t timed.

This is where experiences like Cesarine get it right. Built around the idea that Italian culture lives in family kitchens, This platforms connects travellers with local hosts who open their homes and cook the recipes they actually grew up with.

In Milan, that might mean sitting near Fondazione Prada with a Cesarina called Sissi, tasting mountain dishes like pizzoccheri that link the city to Olympic regions such as Bormio and Livigno. Or cooking saffron risotto and ossobuco with Nicoletta and her husband Fabio, learning recipes shaped by Sunday lunches rather than trends. Two Cesarines that will be pleased to have you at their table.

Nothing here is staged. No one is performing Italian-ness. The food isn’t trying to impress. It just is what it is, and that’s precisely why it works.

The irony is that this kind of intimacy is exactly what Under the Stars was missing. Real chemistry, on screen or in real life, rarely comes from perfection. It comes from shared moments that aren’t particularly glamorous. Cooking together. Eating slowly. Talking about nothing important at all.

As Milan prepares to welcome the world for the Winter Olympics, travellers face a familiar choice. Italy can be consumed like a beautifully shot film that you forget a week later. Or it can be experienced the way Italians have always experienced it: through hospitality, generosity and a good meal that lasts longer than planned.

Italy doesn’t need better scenery. It already has that covered. What it needs is visitors willing to sit down, listen and stay a little longer. That, at least, is one way to guarantee your Italian story won’t flop.