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.
The human touch
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.
The Duomo was only 10 minutes away. Luckily, I had a second opportunity to visit it, because, unlike my virtual travel assistant, Ms. Basso had sent me a link to prebook my tickets. (Earlier, when I asked the A.I. assistant if it had the capability to book ahead, it referred me to the Expedia app.) With advance tickets, I was able to spend more than an hour admiring the cathedral’s stunning stained glass windows and archaeological ruins, rather than being stuck in line.
In general, Ms. Basso’s itinerary was easier to follow as each stop was a short distance from the next, allowing more time to explore the sites. She also marked out places to visit en route to different sites, like the Villa Invernizzi, a mansion with a garden that is home to a flamboyance of pink flamingos.