Until a few years ago, planning a holiday followed two fairly clear paths: on the one hand there were those who went into a travel agency and entrusted the construction of the itinerary to a professional, on the other those who preferred do-it-yourself, with days spent among reviews, maps, comparators, blogs, forums, screenshots, saved links and messages to friends who had already been to that destination. Today, however, more and more often everything begins with a question addressed to ChatGPT, Gemini, Claude or another artificial intelligence assistant: “can you suggest a quiet hotel near the Colosseum, suitable for a weekend as a couple and not too touristy?”.
It is a silent revolution, but already very concrete. According to data released by the Travel Innovation Observatory of the Polytechnic University of Milan, one in three Italian travelers uses generative AI tools to define itineraries and search for experiences, and 85 percent of those who use them consider them useful or even fundamental. Over the same period, Google Trends reports a 300 percent increase in interest in “AI travel assistant” between April and June 2026.
The promise is clear: less time wasted comparing options, more suggestions already sorted based on tastes, budget, dates, location, travel style and personal expectations. In theory, artificial intelligence can become the ideal consultant, always available, very fast and capable of transforming a vague request into a structured proposal. In practice, however, the difference between a truly useful itinerary and a list of generic advice depends on one very simple thing: the quality of the question.
The dream of the perfect journey generated by AI
The desire to rely on artificial intelligence arises from a real need. Organizing a trip requires time, attention, the ability to filter information and a certain amount of patience. Choosing an area to sleep in, understanding whether a hotel is really comfortable or just well described, evaluating distances, comparing prices, checking openings, reservations, cancellation conditions and recent reviews can transform even a weekend into a small organizational undertaking.
AI promises to simplify all this, building personalized and seemingly ready-made responses. According to Booking.com’s Travel Predictions 2026, 57 percent of travelers imagine “delegating the planning of a surprising and little-traveled travel itinerary to Artificial Intelligence, which is in line with their desires”.
The point is that an itinerary generated in a few seconds may seem perfect, but it may also be based on outdated information, underestimated distances, prices that are no longer valid, descriptions that are too generic or suggestions that don’t really take into account the traveler’s concrete needs. The Smartness press release highlights how, globally, there remains strong concern about the correctness of the information provided by artificial intelligence tools, while 24 percent of users say they are faced with too vast a choice and options that are not always significant for their trip.
The problem is not AI, but how it is used
The risk, therefore, is not so much using artificial intelligence to organize a holiday, but using it badly. Asking “give me an itinerary for Rome” or “recommend a hotel in Paris” almost always means getting a generic answer, built on already well-known places, standard formulas and suggestions that could be suitable for anyone. AI works best when given context, constraints, preferences, and even limits.
“AI can drastically reduce the time needed to choose a destination, compare facilities and build itineraries. But the quality of the result depends on three factors: data, well-formulated prompts and human control”, explains Luca Rodella, CEO of Smartness, a technological platform for hospitality that integrates artificial intelligence and automation to support hotels and accommodation facilities. “Without these elements, the risk is receiving apparently personalized suggestions, but in reality homologated, incomplete or built on unrealistic expectations”.
The key word is prompt, that is, the request that is written to the AI assistant. An effective prompt should not limit itself to indicating destination and dates, but should resemble the information you would give to a travel consultant: who is going, with what budget, at what pace, with what interests, with what needs, which experiences you want to live and which ones you want to avoid.
How do you ask the AI to organize a trip
The difference between a useful answer and a mediocre answer is in the details. Telling the AI that you are traveling as a couple, with children, with elderly parents or alone completely changes the construction of the itinerary. Specifying whether you will arrive by train, car or plane allows you to avoid uncomfortable areas. Indicating the maximum budget for the hotel, the type of neighborhood desired, willingness to walk, eating habits, allergies, experiences already had and those you don’t want to repeat allows you to obtain a result that is much more in line with reality.
An effective example could be: “Act as a travel consultant. We are two people, we want to spend three days in Rome from 10 to 12 July, maximum budget 300 euros per night for the hotel, we will arrive by train, we prefer central areas but not too chaotic in the evening, we are interested in local restaurants, museums and we want to get around on foot. Before suggesting hotels or activities, tell me which information may not be updated and what I need to check before booking”.
It is precisely the last part that is decisive, because it forces the AI to declare its limits and remind the user which aspects need to be controlled. Prices, availability, opening hours, actual distances, cancellation conditions and recent reviews should always be checked before booking. AI can be an excellent starting point, but it should not become the sole source on which to base a travel decision.
Hotels also need to learn to speak to artificial intelligence
The transformation does not only affect travellers, but also hotels, holiday homes and accommodation facilities. If people begin to discover destinations, itineraries and hotels through responses generated by AI, it will no longer be enough to be online, have an updated website or appear well on Google. It must be understandable, relevant and readable even by the new response engines.
It is the principle of GEO, Generative Engine Optimization, which supports traditional SEO and aims to make content, data and digital sources more easily interpretable by tools such as ChatGPT, Gemini or Perplexity. For an accommodation facility it means stopping relying only on generic formulas such as “strategic position” or “welcoming atmosphere” and starting to communicate really useful information: neighbourhood, real distances, connections, services for families, accessibility, atmosphere of the area, type of ideal guest.
In other words, if a hotel wants to be suggested by AI to a traveler looking for a quiet, central but not chaotic stay, close to transport and suitable for a family, it must provide clear data on precisely these aspects. It is no longer enough to exist online: you need to be described in the right way.
Technology helps, but does not replace human judgment
Artificial intelligence can enormously shorten search times, suggest alternatives that hadn’t been thought of, build thematic itineraries, compare neighborhoods, prioritize and help the traveler clarify his ideas. But it still cannot completely replace human verification, especially when practical elements such as updated prices, availability, booking conditions, security, transportation and real quality of experiences come into play.
“Artificial intelligence does not work like a magic wand: it works when it has reliable data, clear objectives and strategic supervision. It applies to a traveler who asks for an itinerary, but it also applies to a hotel that uses AI to define prices or increase its visibility. Technology can reduce manual work and speed up decisions, but attention must be paid to it so that expectations correspond to reality”, concludes Rodella.
The future of travel, therefore, will not simply be delegated to machines. Rather, it will be a dialogue between artificial intelligence and human intelligence, between automation and control, between speed and common sense. AI can suggest a route, but the traveler still needs to know what they really want, what compromises they are willing to accept, and what details cannot be left to chance. Because a successful holiday does not arise from the quickest answer, but from the most precise question.
