I wasn’t exactly sure what to expect from the itinerary my travel adviser had put together in a mere five seconds, but when I arrived in Milan’s central Piazza del Duomo, the cathedral glistening under the midday sun, I anticipated being swept into the city’s frenetic rhythm. Instead, I found myself in the middle of a relatively empty square, surrounded by shuttered stores and cafes.

“Why didn’t you tell me today was a public holiday in Milan?” I texted my adviser.

“I’m sorry, I didn’t realize that you were planning to visit Milan on May 1,” the adviser responded. “As a virtual travel assistant, I try to provide as much information as possible, but sometimes I miss something. I apologize for any inconvenience this may have caused you.”

I felt bad, as if I had hurt someone’s feelings, and had to remind myself that I wasn’t talking to a human. It was my first trip to Milan, and I was using the opportunity to try out the beta version of Expedia’s travel-planning chatbot powered by ChatGPT.

Travel companies are already using artificial intelligence to help with customer service and bookings, but now services like Kayak and Expedia are experimenting with A.I. assistants to help people find places to go and stay. I decided to put Expedia’s service to the test by comparing its itinerary with one prepared by a human adviser. “I have one day to visit Milan. Where should I go?” I asked it. “What should I see?”

The virtual itinerary

Perhaps my expectations were too high to expect the A.I. assistant to know that my plans coincided with a national holiday. I apologized for snapping and asked it to recommend a nearby lunch spot that was open. It suggested Galleria, a restaurant at the grand Galleria Vittorio Emanuele II shopping arcade, which was already on my ChatGPT-generated itinerary. The stunning, glass-covered, 19th-century complex is a Milan landmark, filled with luxury boutiques and restaurants. Did I need a reservation? My travel assistant recommended one, but since the restaurant was a short walk away, I decided to try my luck.

When I arrived, there was a long line of tourists eyeing the wood-fired pizzas and colorful pasta plates on the outside tables. I checked in with the host and asked if there was a table for one. Immediately, a waiter motioned for me to follow him inside, where he pulled up a chair next to a cozy corner spot.

At a nearby table, an American couple scrolled through their phones, looking for a place to have dinner, even before they had finished lunch. “There’s a traditional Milanese restaurant close to the hotel, but it has mixed reviews,” the woman told her partner. At that moment, I was grateful that my A.I. guide had already narrowed down my dinner options and spared me the burden of having to wade through the endless possibilities presented by Google. It also allowed me to put down my phone and soak in the atmosphere as I enjoyed my delicious spicy salami pizza and a glass of the house Chianti Classico wine.

After window shopping in the Scala area, it was time to climb the Duomo di Milano, Milan’s main attraction, a cathedral renowned for its expansive rooftop with its intricate Gothic-style stone spires and gargoyles and stunning views of the city against a backdrop of the snow-capped Alps. But when I got there, I hit another long line, and after such a heavy lunch, I didn’t have the patience to wait.

So I moved on to the next stop: the Pinacoteca di Brera art museum. But when I checked the opening hours through Google, it appeared to be closed for the holiday.

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.

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.

While my A.I. assistant was equipped with an expansive database and programmed to think and respond like a human, I didn’t completely trust its judgment and at times felt compelled to do my own research. ChatGPT only has access to information up to 2021, and a lot has changed in the travel industry since then. Still, I thought my assistant struck a good balance between suggesting must-see landmarks and lesser-known parts of the city. The key was to frame the questions as directly as possible. I also appreciated how it responded instantly and was available round the clock.

A friend’s travel advice

Still, no travel experience is complete without the recommendation of a local friend. Mine sent me a list of places, including Casa Atellani, Museo Poldi Pezzoli and Villa Necchi Campiglio, that wasn’t featured on either of my advisers’ itineraries. But with limited time before my train home, I only had time to visit one. I chose his lunch recommendation.

Rita & Antonio on Via Giacomo Puccini had the vibe of a traditional establishment, with delicious food at reasonable prices. I was feeling adventurous and asked the waiter to pick a dish. Within minutes he was back with a giant plate of steaming seafood pasta that he placed on the table with a grin.

“You will like this,” he said. And he was right: It was truly delicious, a taste of authentic Italy.

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