In Milan, putting an AI travel advisor to the test

plan their trips. Travel companies are using artificial intelligence to help with customer service and bookings. Services such as Kayak and Expedia are experimenting with AI assistants to help people plan their trips.

In Milan, putting an AI travel advisor to the test


The AI assistant had a vast database and was programmed to respond and think like a person, but its judgment couldn't be trusted.

What I expected from the


My travel advisor had compiled the itinerary in just five seconds. However, when I arrived at my destination in


The central Piazza del Duomo of, with its cathedral sparkling in the midday sun. I expected to be swept up into the frenetic pace of the city. Instead, I was in a square surrounded by closed cafes and stores. Why didn't I know today was a holiday in Milan? I texted my adviser. The advisor replied, "I'm so sorry. I didn't know that you planned to visit Milan on the 1st of May." As a virtual assistant for travel, I do my best to give as much information as I can, but I sometimes miss something. I apologize for any inconvenience caused.

I felt bad as if I'd hurt someone's feeling and had to remind my self that I wasn’t talking to a real person. It was my very first trip to Milan and I wanted to test out the beta version.


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Travel companies already use artificial intelligence for customer service and bookings. Now, services like Kayak and Expedia have begun experimenting with AI assistants that can help users find the best places to stay and go. Expedia's services were put to the test when I compared their itinerary to one created by a human travel advisor. I have only one day to spend in Milan. What should I do? "Where should I go?" What should I look at?

Virtual Tour

Maybe my expectations were too high for the AI assistant to be able to tell that my plans coincided on a national holiday. I apologized for taking a picture and asked the AI assistant to recommend an open lunch place nearby. It recommended Galleria, the restaurant in the Galleria Vittorio Emanuele II, which I had already put on my ChatGPT itinerary. This 19th-century complex, covered in glass, is a landmark of Milan, full of luxury shops and restaurants. Do I need to make a reservation? Since the restaurant was only a few minutes walk from my hotel, I decided to take a chance. There was a line of tourists waiting outside the restaurant to see the colorful pasta dishes and wood-fired Pizzas. I asked the host if there was room at a table. A waiter gestured to me to follow him into the restaurant, where he sat down in a corner seat. A couple of Americans were scrolling through their phones at a table nearby, searching for a restaurant to eat dinner before they finished their lunch. The woman said to her partner, "There is a traditional Milanese Restaurant close to the Hotel but it has mixed ratings." In that moment, my AI guide narrowed my options for dinner and saved me from having to wade my way through Google's endless possibilities. This allowed me to enjoy my spicy salami and house Chianti Classico wines while putting down my phone. After window-shopping in the Scala district, it was time for the Duomo di Milano. This is Milan's most famous attraction. It is a cathedral renowned by its extensive rooftop, with its intricate Gothic style stone spires, gargoyles, and stunning views over the city and snow-capped Alps. After a big lunch, the line was long and I did not have patience to wait. Then I went to the Pinacoteca Di Brera, an art museum. When I looked up the Google opening hours, it was closed. As it was still too early to visit the other aperitivo places on my list, I asked ChatGPT for some of Milan's hidden gems. The Porta Ticinese was one of the options it suggested. It described this area as "a trendy area with vintage stores, street art, and a vibrant nightlife." ChatGPT suggested the San Maurizio al Monastero Maggiore. This church is filled with beautiful, vibrantly painted frescoes depicting stories of saints, scenes from the Bible, and other historical events. It was peaceful and there were no queues. The final stop on the itinerary of my virtual assistant, Locanda alla Scala in Milan, served a traditional (and delicious!) veal-chop meal. ChatGPT recommended four mid-range boutique hotels, each of which had a brief description. Normaly, I'd do extensive research on hotels before booking them - read reviews and ask locals for recommendations. This was an experiment so I trusted the travel assistant. On my first night, I chose the Hotel Milano Scala. ChatGPT described it as a boutique with a "focus on sustainability and wellbeing." The hotel was located in a central area, within walking distance to many attractions. The staff were friendly and the room was clean and comfortable. It was claimed that the filtration system provided "excellent indoor air" quality. The hotel was a boutique, but it felt crowded, especially at breakfast when large groups of people arrived at the same time.

The human touch

The Locanda Pandenus was a great choice for my second night. It felt like a home, and I stayed there on the recommendation from Franziska Basso. She is a travel designer based in Milan, working with Dreamsteam Exclusive Travel, which is a member of Virtuoso's luxury network. It was quiet and cozy, with only four bedrooms accessible by a staircase located above a restaurant. Despite its central location, in the Brera district, which is full of restaurants, boutiques and art galleries, the hotel felt isolated from the busy city. Basso, unlike my virtual assistant, had sent me an email with a link for pre-booking my tickets. When I had asked my AI assistant earlier if she could book in advance, she had referred me the Expedia app. Basso's itinerary made it easier to follow, as the stops were close together, giving me more time to explore each site. She marked places to stop at en route, like the Villa Invernizzi with its garden full of pink flamingos. Most visitors to Milan flock to the "Last Supper" mural, but few make the trip to the Casa degli Atellani, a private residence in Milan's lush gardens dating back to the 15th century. As I sat on the lawn in front of da Vinci’s original vine stock, I was transported back to Renaissance times as I listened an audio guide. It was now golden hour and I went to the Navigli canals for an aperitivo. This is the Italian tradition where you drink a little something before dinner. This is where I reflect on my journey and compare the two itinerary options. Basso's services were no doubt more personalized, underlining the importance of human contact. She asked me questions about my preferences before sending me her recommendations, and I trusted the advice she gave me, knowing that she was an experienced local. ChatGPT has only access to data up to 2021. Since then, the travel industry has evolved significantly. My assistant did a great job of balancing the suggestions between must-see attractions and lesser-known areas. It was important to ask the questions in a direct manner. It was also great that it was available 24/7 and responded immediately.

Travel advice from a friend

No travel experience would be complete without a recommendation from a local. My friend sent me a list that included Casa Atellani and Museo Poldi Pezzoli, as well as Villa Necchi Campiglio. These places were not on my advisors' itinerary. Due to my limited time, I could only visit one. I went for his recommendation. Rita & Antonio, on Via Giacomo Puccini, had a feeling of a traditional restaurant with great food and reasonable prices. I asked the waiter for a recommendation. He returned with a huge plate of seafood pasta and placed it on the table, grinning. He said, "You'll like this." He was right, it was delicious and authentically Italian.