In Milan, putting an AI travel advisor to the test
It was too early to try the aperitivo spots that followed on my list, so I asked ChatGPT to show me some of Milan’s “hidden gems”. It came up with several options, including the Porta Ticinese, which described it as a “trendy area with vintage shops, street art, and vibrant nightlife.”
But I was eager to see some art and history and opted for another ChatGPT suggestion: the San Maurizio al Monastero Maggiore, a church full of stunning, vividly painted frescoes depicting 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 Locanda alla Scala, the last stop on my virtual assistant’s route.
I had asked ChatGPT to recommend a mid-range boutique hotel for the night, and it offered four options, each with a one-sentence description. Normally I would do extensive research before booking a hotel room – read reviews and ask local friends for recommendations. But this was an experiment after all, so I trusted the travel assistant and opted for the on my first night Hotel Milan Scalawhich described ChatGPT as a boutique hotel with “a focus on sustainability and well-being”.
The hotel had a convenient central location within walking distance of many major attractions. The staff were friendly and the room was comfortable and clean and claimed to have “excellent indoor air quality” provided by a filtration system. But despite being a small boutique hotel, it felt overrun with tourists, especially at breakfast, when groups arrived in the dining area at the same time.
The human measure
In contrast, the Locanda Pandenuswhere I stayed the second night, on the recommendation of Franziska Basso, a Milan-based travel designer for Exclusive Dreamsteam trips (a member of the luxury Virtuoso network), felt more like staying in a home than a hotel. With only four bedrooms, reached by a small staircase above a restaurant, it was quiet and cozy and felt secluded from the hustle and bustle of the city, despite its central location in the charming Brera neighborhood, full of boutiques, art galleries and restaurants.