What happens when holidays plan themselves?

Organising a holiday is one of the few ways I can turn five days of rest into a part-time administrative position. I open seventeen browser tabs, compare the same flight six times and eventually return to the first one after its price has risen. There will be an airline tab, a hotel tab and several restaurants I save with great enthusiasm before forgetting they exist. Somewhere in the middle, I will send screenshots to a WhatsApp group in which everybody has an opinion but nobody wants to make the booking. From Cyprus, spontaneity also has geographical limits. We cannot board a train after work and wake up in another country. Nearly every escape begins with a flight, an airport and the careful calculation of whether a 6am departure is worth the emotional damage. In 10 years, all this may appear rather old-fashioned. By 2036, I may simply tell an artificial-intelligence agent that I need five days away, somewhere cooler than Limassol, with a direct flight, a sea view and a budget I would prefer not to discuss aloud. It will already know that I dislike early departures, avoid hotels with suspicious carpets and do not consider a property “close to the beach” when reaching the beach requires a rental car. The agent will search, compare, book and pay. If the flight is cancelled, it may rearrange the hotel, transfer and dinner reservation before I have even discovered there is a problem. My holiday could be booked before I overthought it. This is the most believable part of the future because it has already begun. In April, European travel group eDreams ODIGEO launched an AI booking tool that turns an ordinary conversation into a personalised, bookable itinerary. A month later, Amsterdam-based Booking.com introduced new AI tools allowing travellers to search for rental cars through ChatGPT. The change sounds small until one considers what disappears. There are no blue links, sponsored results or five identical hotel pages. I tell an agent what kind of trip I want and allow it to negotiate with the internet on my behalf. Scott Fleming, president of the travel practice at Aon, described the prospect neatly when he said, “My agent will know the places I like, my budget, my risk tolerances.” Presumably, it will also know my passport details, bank balance, medical requirements, loyalty points and the precise amount of legroom necessary to keep me pleasant. This is the price of convenience. To plan the perfect holiday, the agent must know me with slightly alarming intimacy. The same information that helps it find a trip I can afford may also reveal what I could be persuaded to pay. Under EU consumer rules, businesses may use algorithms to personalise prices according to browsing behaviour and preferences, although they must tell customers when automated decision-making has been used. By 2036, my agent may know not only that I want to visit Paris, but that after searching for Paris six times at 11.45pm, I am emotionally ready to pay another €80. It may also occasionally be wrong, although presumably in very confident language. A 2026 Spanish study examined what happened when AI-generated travel plans contained plausible but false information. Unsurprisingly, the errors weakened the usefulness and trust people placed in the recommendations. An invented historical date is inconvenient. An invented ferry is considerably less amusing when one is standing at a port with two suitcases and no boat. The airport itself may also become less visible, although it will probably know far more about us. Hermes Airports is investing more than €170 million to make Cyprus’ airports larger. The expansion project will lift their combined annual capacity beyond 17 million passengers. That is the familiar answer to growth: more gates, passport-control positions, baggage belts and space in which to stand behind somebody who appears surprised that liquids are restricted. However, the longer-term answer may be to remove part of the airport from the airport. Identity checks could take place on a phone before leaving home. A bag might be collected in the city and reappear at the destination. An AI system could calculate when I should leave, direct me towards the quietest entrance and warn me that the coffee queue is moving more slowly than security. In April 2026, international digital-identity trials showed travellers moving through different stages of a journey without repeatedly presenting documents. Identity stored in a digital wallet was reused across airlines and airports, while biometrics replaced manual checks. Meanwhile, the European Commission has proposed an EU travel app through which travellers could store digital versions of passports or identity cards and submit them for advance checks before entering or leaving the Schengen area. Cyprus is not yet in Schengen. However, a Commission report adopted on July 14 delivered a positive assessment of the island’s technical preparedness, according to the latest Cyprus update. It is not a final accession decision, but it brings the island a little closer to the increasingly digital European journey. By 2036, therefore, my face may become my passport and boarding pass. The airport will recognise me, confirm that I am allowed to travel and direct me towards the gate. Europeans remain cautious about biometrics, according to IATA’s 2025 survey. This seems fair. A lost passport can be cancelled. My face is already rather committed to the role. The airport of the future may contain fewer desks but more invisible decisions. An algorithm may decide whether I need an additional check or whether my connection is too ambitious. Hopefully, it will reach the second conclusion before I book it. Meanwhile, entering a country may become easier just as entering a destination becomes more complicated. Venice already charges day visitors on selected busy dates. Its mayor is now considering a demand-based system under which the fee could rise to €50 when bookings pass certain thresholds, according to the latest Venice proposal. By 2036, therefore, booking a city break may require booking the city itself. Famous places could operate more like flights, with a fixed number of spaces, cheaper entry during quiet periods and prices that rise with demand. My AI agent may not merely reserve a hotel in Rome. It may negotiate the hour at which I am permitted to approach the Trevi Fountain. AI was supposed to help us discover overlooked places. It may do the opposite. A Barcelona study by a University of Lleida researcher found that ChatGPT recommended a smaller and more geographically concentrated collection of attractions than those tourists shared on Instagram. Millions of people may receive beautifully personalised itineraries, only to discover that they have all been sent to the same famous square. Climate will make the choices more complicated. A future holiday may be planned not around where the weather is warm, but around where it remains possible to walk outside without immediately searching for shade. The European Commission’s Joint Research Centre has modelled how rising temperatures could reshape tourism. Its climate projections show southern coastal regions losing almost 10 per cent of summer visitors under higher-warming scenarios, while northern coasts gain demand. Cyprus was among the areas projected to experience some of the largest declines. That does not necessarily mean people stop coming. They may simply arrive in April, October or winter. By 2036, July could become the new low season in parts of the Mediterranean, not because the beaches have disappeared but because lying on one at midday no longer feels recreational. My AI agent could check heat, wildfire danger, water availability and crowding before suggesting a destination. It may quietly move the walking tour to 7am and reserve the afternoon for activities involving air conditioning. The route will change too. Mainland Europeans may replace more short flights with trains under the Commission’s rail plan, which aims to complete a faster cross-border network by 2040. Cyprus, being inconveniently surrounded by sea, will remain rather attached to the aeroplane. The aircraft may look familiar, but what enters its tanks should not. Under EU fuel rules, sustainable aviation fuel must account for at least 42 per cent of fuel supplied at EU airports from 2045, compared with 2 per cent in 2025. Cleaner flying may be more expensive, meaning the AI agent could spend considerably more time searching for the least alarming fare. That may be the central contradiction of travel in 2036. It will become easier and more organised, while requiring more data, more permissions and perhaps more money. Still, much of it sounds wonderful. I will not miss printing boarding passes, entering the same passport number four times or discovering at midnight that the airport transfer was never confirmed. However, the imperfections of travel are often where the story begins. We take a wrong turn and find a cafe. We ignore the itinerary because the sea looks better than the museum. We stay for another coffee and miss something we were apparently supposed to see. An AI agent may organise the perfect holiday. My contribution will be gently disobeying it. It can book the trip. I am still choosing the detour.