In Milan, Putting an A.I. Travel Adviser to the Test

It was too early to try the aperitivo spots that followed on my list, so I asked ChatGPT to show me a few of Milan’s “hidden gems.” It came up with several options, including the Porta Ticinese, which it described as a “trendy area with vintage shops, street art and a lively nightlife.”

But I was itching to see some art and history and opted for another ChatGPT suggestion: the San Maurizio al Monastero Maggiore, a church filled with stunning, vividly painted frescoes that depict stories of saints and scenes from the Bible. There were no lines, and it was a peaceful way to wind down the day before the traditional (and delicious) Milanese veal chop dinner that awaited at Locanda alla Scala, the final stop on my virtual assistant’s itinerary.

I had asked ChatGPT to recommend a midrange boutique hotel for the night and it provided four options, each with a one-sentence description. Normally, I would carry out extensive research before booking a hotel room — reading reviews and asking local friends for recommendations. But this was, after all, an experiment, so I put my trust in the travel assistant and opted on my first night for the Hotel Milano Scala, which ChatGPT described as a boutique hotel with “a focus on sustainability and wellness.”

The hotel had a convenient central location within walking distance of many major attractions. The staff was friendly, and the room was comfortable and clean, claiming to have “excellent indoor air quality,” provided by a filtration system. But despite being a small boutique hotel, it felt overrun by tourists, particularly at breakfast, when groups arrived in the dining room at the same time.

In contrast, the Locanda Pandenus, where I stayed the second night, on the recommendation of Franziska Basso, a Milan-based travel designer for Dreamsteam Exclusive Travel (a member of the luxury Virtuoso network), felt more like staying in a home than a hotel. With just four bedrooms, reached by a small staircase above a restaurant, it was calm and cozy and felt cut off from the bustle of the city, despite its central location in the charming Brera neighborhood, full of boutiques, art galleries and restaurants.

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