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 it described as a “trendy neighborhood 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 beautiful, vividly painted frescoes depicting stories of saints and scenes from the Bible. There were no lines, and it was a low-key way to wind down the day before the traditional (and delicious) Milanese veal chop dinner waiting at Locanda alla Scala, the last stop on my virtual assistant’s itinerary.
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 relied on the travel assistant and on my first night opted for 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 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 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 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.
The Duomo was only a 10 minute drive away. Luckily I had a second chance to visit because unlike my virtual travel assistant, Ms. Basso had sent me a link to pre-book my tickets. (Earlier, when I asked the AI assistant if it had the option to book ahead, it directed me to the Expedia app.) With pre-booked tickets, I was able to spend more than an hour admiring the beautiful stained glass windows. stained glass windows and archaeological ruins of the cathedral, instead of being stuck in line.
Overall, Mrs. Basso’s itinerary was easier to follow because each stop was a short distance from the next, allowing more time to explore the sites. She also mapped out places to visit on the way to various locations, such as the Villa Invernizzi, a country house with a garden that is home to a flamboyant pink flamingo.
