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.

She also made sure to take me off the beaten path, sending me on a 25-minute walk outside the touristy city center to Leonardo da Vinci’s vineyard. While most visitors to Milan line up to see the artist’s mural “The Last Supper,” few venture out to the 15th-century private Milanese residence tucked away in the lush gardens of the Casa degli Atellani. I sat in the garden in front of Leonardo’s original vine stock and was transported to the Renaissance as I listened to an audio guide about the property and legends involving the artist.

By the time I finished, it was golden hour, and I headed to the canals of the Navigli district for an aperitivo, the Italian tradition of a pre-dinner drink with a small bite. Here, I reflected on my trip and how the two itineraries measured up. Ms. Basso’s service no doubt felt more tailored, highlighting the importance of human interaction. Before sending me her suggestions, she asked me specific questions about my preferences, and I trusted her guidance, knowing she was experienced and a local.