Going somewhere new is exciting, especially to a place you have never seen before. But arriving without a plan or any real sense of the area turns the trip into a gamble: you might stumble on a good restaurant, but you might also book a hotel in an area that gets noisy after dark. You might randomly discover a beautiful street, but you might also miss an iconic landmark.
There is a better way to avoid that gamble, one that skips the hours normally spent researching and building a plan yourself: an AI assistant. Regardless of whether you prefer ChatGPT, Gemini, or another one, it has become a genuinely useful research partner for travel. Join us as we cover what it can help you with, and just as importantly, where it still falls short.
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How to build the trip with AI
First things first: before getting into how to use an AI assistant to plan a trip, it helps to know what it cannot do. It has no way to find or book flights or tickets, and no access to live information like today’s opening hours, current ticket availability, or whether a restaurant is booked out this weekend. Anything that changes day to day still needs a manual check.
What it can do well is gather specifics: which landmarks are worth the trip, which spots most visitors miss, what a neighborhood is really like, and which restaurants and hotels are worth booking based on reviews. Put together, that is enough to build a full day-by-day plan of the trip itself.
Mapping out the city’s landmarks
Start with the obvious question: what should you actually go see? Most people use the vaguest version of this question and just type “things to do in [city]”, receiving back a short, generic list they could have found on any homepage.
Instead, request the well-known landmarks alongside a quieter counterpart in the same category. Specify whether you are drawn to something modern or something historic, and whether you want to learn something, immerse yourself in the local culture, or just have fun.
If your time in the city is limited, say that too, and ask specifically about skip-the-line access, private guides, or the most time-efficient order to see everything, since a traveler with two days available needs a different answer than one with a week. Such an approach gives you a more detailed and diverse response.
For example, if you are planning a trip to Barcelona, a more detailed request will give you not just a generic recommendation to visit the Sagrada Família, but also suggest a lesser-known Gaudí building like Bellesguard, built on the site of a medieval castle, carrying the same architectural detail with almost no crowds.
Learning the city’s basics
Knowing what to see is only half the plan. Once you have a list of places worth visiting, the next step is learning the basics of the city itself. This is the information anyone would need before arriving.
- Neighborhoods: Choosing a neighborhood to stay in usually means comparing several areas of the city, each with its own character and set of logistics. AI can filter the neighborhoods that are close to the main sights and indicate those that require a bus or train ride to reach them. It is also worthwhile to ask what the tradeoffs are: a convenient central area, for example, might mean noisy evenings.
- Transportation: An AI tool can lay out what transportation exists in a city, and then explain which option actually makes sense there. For a traveler who values comfort and time over cost, that often means asking specifically about private drivers and car services rather than public transit, and whether a fixed-rate airport transfer is worth arranging in advance instead of relying on a taxi rank.
- Local culture: Using AI is a fast way to pick up on the local culture before you arrive, starting with the food, what the local cuisine is like and which dishes define it, along with how tipping works. You can learn about dress expectations at upscale restaurants or private clubs, which hours shops and restaurants tend to close for a midday break, and which plug adapter you will need.
Having this information beforehand means every choice that follows: the hotel, the restaurant, the way you get around, is one you are making with real context instead of guessing.
Choosing hotels and restaurants
Once you decide which area of the city you will be staying in, the next step is picking the actual hotels and restaurants. AI is useful here, too, because it reads patterns very well.
Ask it to find well-reviewed hotels or restaurants in that area. Then ask it to audit the reviews: what comes up repeatedly, good and bad. This way, you will not base your decision on the star rating alone. A hotel might have a great location and a high average score, but if a dozen reviews independently mention street noise at night, that is worth knowing before you book. The same pattern-reading can also catch the good details, like a specific dish or menu item that keeps getting singled out for praise.
Building a day-by-day itinerary
An AI assistant can also turn everything it gathers into a day-by-day plan. But to build a good plan, the assistant needs more than just the destination and the length of the trip.
Start by creating a “traveler’s profile’ your assistant can use: how many people are going; what your ages are; whether you prefer a packed schedule or a more relaxed one; and any real constraints that would shape the trip, like limited walking ability, young kids who need downtime, or a fixed return time each evening.
If the trip is built around a business commitment, say so, and give it the fixed meeting days or work hours so the itinerary works around them instead of assuming every day is free. Add the details that you have already decided on, like where you are staying, as well as your preferences and interests.
With that information in hand, tell the assistant directly to keep each day’s stops within the same neighborhood, instead of spreading them across the city. Without that detail, AI might come up with a plan that includes places all over the city. Such plans usually involve a lot of commuting and backtracking, and not much of anything else.
Once a draft of a plan exists, ask the assistant to check its own work: whether the timing between stops is realistic, whether anything is likely to be closed that day, and whether any single day is overloaded. AI is far better at catching a problem that is already on the page than at building a flawless plan from the ground up.
Where AI stops being useful
AI is a useful research partner for almost everything covered so far, but flights are the one area where it does not hold up. It has no access to live fares, no way to check real-time seat availability, and no connection to a booking system, so it cannot tell you what a business-class seat actually costs today or whether one is even available on the flight you want. Any price it gives you is a guess built from old patterns, not something pulled from the current market, and it will often sound confident about that guess in a way that does not match how reliable it actually is.
This is where working with an actual expert makes the difference. At AranGrant, we have access to unpublished fares that never show up in a standard search, often at a meaningfully better value than the public price. Our team of experts can also tell you exactly what you are booking: whether the seat is lie-flat, what the meal service looks like, what entertainment is available on board, so the flight itself is as comfortable as the whole trip you are planning.
Putting it all into one prompt
The prompt below brings every part of this together into a single request you can copy directly into an AI assistant.
I am traveling to [destination] for [number of days] in [month]. Here is who is traveling: [number of people, age or ages, pace preference, and whether this is a first visit to the destination or a return trip].
Give me the city’s major landmarks along with two or three less-visited alternatives in the same category. I am drawn to [something modern or something historic], and I want to [have fun, learn something, or immerse myself in the local culture]. My time here is limited, so tell me about skip-the-line access, private guides, and the most time-efficient order to see everything.
Break down the city by neighborhoods: which are close to the main sights, which require a commute to reach them, and what the trade-offs are between them.
Tell me what transportation options exist, including private drivers or car services, whether a fixed-rate airport transfer is worth arranging in advance instead of relying on a taxi rank, and roughly what each option should cost.
Tell me what the local food is like and which dishes define it, how tipping works, dress expectations at upscale restaurants or private clubs, which hours shops and restaurants tend to close for a midday break, which plug adapter I will need, and anything else a first-time visitor would want to know.
Recommend a few well-reviewed restaurants and hotels in the neighborhoods that fit my trip, in different price ranges, and summarize what reviewers consistently say about each, good and bad.
Build a day-by-day itinerary grouped by neighborhood instead of spread across the city, then check your own plan for unrealistic timing, anything likely to be closed, or any overloaded day. [If this trip is built around a business commitment on specific dates or hours, add that constraint here so the itinerary works around it.]
Although this prompt produces solid results, treat it as a starting point. Change the prompt how you see fit, argue with the answers, ask AI to go deeper on whatever matters most to you. The more you push, the more useful replies you get. Just remember to double-check anything time-sensitive before you rely on it.
