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In Milan, Putting AI Travel Assistants to the Test

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

But I was itching to see some art and history and chose 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 a traditional (and delicious) Milanese veal chop dinner awaited Locanda Alla Scala, Last stop on my virtual assistant’s itinerary.

I asked ChatGPT to recommend a midrange boutique hotel for the night and it provided four options, each with a one-sentence description. Normally, I’d do extensive research before booking a hotel room — reading reviews and asking local friends for recommendations. But ultimately, it was an experiment, so I trusted Travel Assistant and on my first night chose Hotel Milano ScalaDescribed by ChatGPT 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. Staff were friendly, and the room was comfortable and clean, boasting “excellent indoor air quality” provided by a filtration system. But despite being a small boutique hotel, it’s overrun by tourists, especially at breakfast, when groups arrive at the dining room at the same time.

In contrast, the Locanda PandanusWhere I stayed the other night, on the recommendation of Franziska Basso, Milan-based travel designer Dreamstime Exclusive Travels (a member of the Luxury Virtuoso network), was more like a home stay than a hotel. With only four bedrooms, accessed by a small staircase above a restaurant, it was quiet and comfortable and felt cut off from the city’s hustle and bustle, despite its central location in the charming Brera neighbourhood, full of boutiques, art galleries and restaurants happened.

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