Milan, the Second Time Around

This was my first year running programs in northern Italy, and I'm so grateful for how it went. I've lived in Milan since the spring of 2025, and when I'm not in the city I'm at one of our homes in Liguria, on Lake Como or up in the Alps. If I had to pick one week that explains what I do here, it would be this one.

It started in Mexico City, with a family I had already hosted there. The parents had been to Milan years ago and honestly weren't impressed. While they were with me in Mexico City I told them about my Milan, the one I live in every day, and they decided to give it another try. This time they brought their grown children. The whole family works in film.

What they asked for

They wanted the things you can't arrange on your own. Artists in their studios, chefs in their kitchens, gallerists in their own living rooms. They spend their lives framing beautiful shots, so the settings had to be beautiful too. They wanted to eat everywhere, from the famous dining rooms to the family trattorias. And they wanted to spend their days with people who actually work in Milan's creative world, not with tour guides.

In Milan they had a suite at The Carlton. But first, the lake.

PhotoCrossing Lake Como by private boat

On the lake

We did Lake Como by boat and by car. One morning two Italian collectors, who take their cars to classic car shows all over Europe, picked us up in a 1950s Mercedes-Benz 220 SE and a Lancia Aurelia B50 convertible and drove us around the lake themselves. By lunch they and my clients were friends.

We skipped Bellagio, which is packed no matter when you go, and walked around the old center of Como instead. The family stayed at Il Sereno. We visited some of the lake's great villas privately, and everyone had a spa treatment to shake off the jet lag.

PhotoThe 1950s Mercedes-Benz 220 SE convertible

In the city

Milan is a city that keeps its best things behind closed doors, so you need someone to open them. We started with fashion, because you can't come to Milan and not. The big houses, of course, but also the smaller finds. We spent a day with a fashion historian, went looking for vintage dealers tucked away in private courtyards, and visited a home that holds an archive of Marni, Prada and Jil Sander.

Then the studios. Veronica Gaido, one of the best photographers in Milan and now a friend, did a long-exposure session with the family in her studio. Another day we went to a working perfume lab in the Navigli for a session on scent.

After one gallery visit, the gallerist invited us next door to her apartment for an aperitivo. She walked us through the pieces she keeps for herself and told us why each one stayed. Afternoons like that are a normal part of how I work with contemporary art through my art advisory.

And we ate, high and low, the way I always do. Langosteria, inside the Fendi building. Al Baretto Sant'Ambrogio, which is where everyone in Milan wanted a table this season. A long, easy lunch at a restored seventeenth-century farmhouse, with the vegetables growing a few steps from the table. Dinner at The Wilde, my club, which used to be the Versace family home. And a lunch under the trees in Parco Sempione on one of those sunny autumn days Milan gets in October.

The doors you can't book

Their week happened to fall during the World's 50 Best Bars awards, which were in Milan this year, so they got into industry events that are closed to the public. I couldn't have bought that for them. It was a favor from friends of mine in Mexico City who own some of the best-known cocktail bars in the world.

The last night was a birthday. We had dinner at what I call the friends' kitchen, a table set right inside an acclaimed restaurant's kitchen, with the chef hosting us as if we were at his house. Truffled risotto, wagyu fillet, and the Rolling Stones and the Doors on the turntable, on the original vinyl. He came over at least three times, and once he brought a pair of his signature glasses for each of the three women.

PhotoThe table inside the chef's kitchen

The next morning the father sent me a message. Everyone was happy, he said, and the dinner felt like sitting at the big table in a friend's home. Then he wrote a line I've held on to.

“Both inspired conception and magnificently executed, without any unnecessary fuss.”

From the client, the morning after

Honestly, I couldn't ask for a better review.

Italy is always in season

Milan is home, but I spend just as much time outside it, and there really isn't a bad month to be up here. There are the smaller cities people tend to skip, like Verona, Monza, Brescia and Bergamo. There are the lakes, and not only Como, but Maggiore, Garda and Iseo too. Venice and Turin are an easy train ride away. Further south you have Alba and the Langhe hills in Piedmont, and over on the coast, Genoa and Savona in Liguria. And then the mountains, the Dolomites and the Alps. Every one of these places deserves its own week, and I hope to write about all of them here eventually.