Some find it exciting, while others see it as a nightmare: planning a holiday takes time, energy and a certain amount of patience—resources we are not always willing to invest. A travel agency could certainly simplify the process, but at the cost of pushing up the budget. So, as true geeks, we considered the alternatives before turning to our best bet: ChatGPT. It is used for almost everything, from wellness advice and work to gourmet recipes, so why not put it to the test as a tour operator for a last-minute holiday?
If you have left it late and have not yet booked your holiday, this guide will show you how to organise a trip with AI by automating the operational stages: research, comparison and planning.
First the prompt, then the suitcase
Planning a trip with AI may seem like a brilliant shortcut… until the result falls short of expectations. Often, however, the problem lies not with the tool itself, but with how we communicate with it. To obtain genuinely useful answers, we need a well-considered prompt.
A structured request allows AI to understand the context more clearly and provide relevant, consistent and personalised results. It is useful to include a few key elements:
- context and objective. Clarify what you are looking for (for example, an itinerary, a selection of destinations or a comparison of options).
- Practical information. Specify the length of the trip, the dates, the budget, the departure city and the number of participants.
- Personal preferences. Seaside, mountains or countryside? Europe, South-East Asia or elsewhere? Tourist destinations or less conventional places? An interest in local food, cultural activities or sport?
The output can then be customised by specifying the response format: a bulleted list, a daily itinerary or a comparison table, as well as the level of detail, such as a brief summary or an in-depth response. The more precise the prompt, the more likely the output is to meet expectations.
Planning a trip with AI: a step-by-step guide using ChatGPT
It is important to understand that when using a conversational model such as ChatGPT for travel or for complex requests that are subjective and involve many variables which are often interdependent, the system has no predefined information about the user: each response is therefore based solely on the data provided during the conversation. Virtual assistants operate using natural language processing: the model interprets the prompt as a text-based request and constructs its response by combining knowledge, inferences and language patterns.
For this reason, the interaction should be structured as an iterative process, in which the user gradually provides specific details to guide the AI in generating relevant suggestions.
A general rule for obtaining a good response is to start with a general request (e.g. ‘I would like to plan a holiday in Europe in August’), to provide context, and then proceed with questions that progressively narrow the scope. In this way, the conversation develops a progressive, adaptive structure in which the AI refines its responses based on the context and previous input.
On holid(AI)y
A practical example
Our summer holiday will therefore have the following parameters.
- Duration: 7 days
- Period: from 10 to 25 August
- Departure: Milan
- Budget: up to €1,500 per person (flight, hotel, meals and activities)
- Preferences: uncrowded beaches, local cuisine, and some light sporting activities (kayaking, hiking)
Planning a trip with AI: a step-by-step guide using ChatGPT
The first step is to choose the destination. AI can provide a list of suitable destinations based on your requirements and analyse their advantages and disadvantages.
Example prompt
Suggest three seaside destinations for a seven-day summer holiday departing from Milan between 10 and 25 August, with a maximum all-inclusive budget of €1,500. The destinations should be relatively uncrowded, offer good food and provide opportunities for light sporting activities. For each one, outline the advantages and disadvantages.
Results
- Slovenian Coast (Piran and Portorož)
- Pros: Calm sea, excellent food, affordable prices
- Cons: It is not an “exotic” destination
- Naxos (Greece)
- Pros: Less touristy beaches, water sports, culinary traditions
- Cons: Connecting flight, high prices in August
- Menorca (Spain)
- Pros: protected natural areas, quiet coves, local cuisine
- Cons: Hiring a car is almost essential
AI PlanningFinding flights and hotels with AI: a faster search
Once you have chosen your destination (in this case Naxos), you can ask AI to identify the best flight and accommodation options. Here too, providing details will help generate a more personalised response. You should therefore clearly specify your maximum budget for flights and hotels, your preferred flight times, the standard of accommodation, any preferred proximity to the beach or town centre, and the review scores to consider. You can also request a comparison of several options, giving you alternatives to assess, and ask it to consider hybrid or alternative solutions, such as combining different modes of transport (for example, flight + ferry).
Example prompt:
Find a flight from Milan to Naxos between 10 and 25 August, with a maximum fare of €350 each way. Also suggest a three-star hotel near the beach, rated above 8 on Booking, for under €100 per night for a double room. Provide at least three options for each, with pros and cons.
Result
- Suggested flight: Milan Malpensa → Athens → Naxos, with a 2-hour layover. Total return fare: €630.
- Suggested hotel: Argo Boutique Hotel, approximately €95 per night, including breakfast, 100 metres from Agios Georgios beach, in a convenient location and with excellent reviews.
Alternatively, AI also suggests more affordable options (such as taking the ferry from Athens to Naxos instead of a domestic flight). In this case, however, the connecting flight was preferred for convenience.
At this point, you can accept the option suggested by the AI or ask for further options. It goes without saying that actual bookings cannot be made, and that you need to visit the official websites before confirming the information.
Planning the itinerary day by day
One of the most common requests made to AI systems is to create a tailored itinerary, alternating activities and relaxation based on the preferences expressed.
Example prompt
Create a seven-day itinerary for Naxos, with a balance of seaside activities, gentle hikes and local cuisine. Avoid overly touristy places and recommend traditional restaurants.
Result (excerpt)
- Relax in Agios Prokopios, dinner at To Elliniko
- Kayaking at Mikri Vigla, lunch at the local kiosk
- Hike up Mount Zas, dinner in the village of Chalki
- Boat trip to Koufonisia
- Visit to Apiranthos and Kitron tasting
- Snorkelling at Plaka Beach
- Walk through the historic centre of Naxos Town
AI for travel: packing your suitcase with the help of ChatGPT
All that remains is to pack our suitcase, and to make sure we do not leave anything essential at home, we let our tour operator guide us once again. Below is a prompt designed to take the planned activities into account. We show you only an extract from the output: the full version also included a list of clothing, personal care items, technology accessories and necessary documents.
Example prompt
Generate a packing list for a seven-day holiday in Naxos in August, including beach trips, hiking and kayaking.
Result (excerpt)
- Lightweight, breathable hiking shoes
- Water shoes or kayaking shoes
- Hiking backpack (20–30L)
- Sun hat or bandana
- Sunglasses with UV protection
- Microfibre beach towel
- Long-sleeved technical top (UV-protective or for hiking)
What does the traveller take away?
L’AI is an excellent assistant, but it is not yet able to decide whether you prefer a room with a sea view or one close to breakfast. Bookings, final checks and definitive choices remain firmly in your hands.
A few good habits, however, never go amiss:
- always check recent reviews across multiple sources (do not take the information at face value).
- Check the flight and accommodation details before clicking ‘Book now’.
- Adapt the itinerary to your own pace: even AI cannot know how keen you will be to get up at 7 a.m. to go kayaking.
In short: you choose the route, but AI is a good navigator… which is still better than nothing.
A ready-to-use prompt
At this point, you have everything you need to turn ChatGPT into your personal travel agent. However, if you are still unsure how to write an effective prompt, below you will find a ready-to-use formula.
Plan a [number]-day summer holiday departing from [City] between [Dates]. Maximum budget: [€], for [all-inclusive/flight+hotel/hotel…]. Preferences: [seaside/mountains/city], [food/sports/cultural/relaxation] activities, comfort level: [basic/mid-range/luxury]. Suggest three less crowded destinations, flights and accommodation, and create a detailed itinerary with restaurant and activity recommendations.
