Planning a Trip with AI: A Practical Guide for Smart Travel

Some find it exciting, others see it as a headache: planning a holiday takes time, energy, and patience—resources you might not always want to spend. Sure, a travel agency could help, but often at the cost of a bloated budget. So, as true geeks, we explored alternatives and turned to our most reliable ally: ChatGPT. We already use it for wellness tips, work help, and gourmet recipes—so why not test it as a tour operator for a last-minute getaway?

For all you procrastinators out there, if you haven’t booked your vacation yet, this guide shows you how to plan a trip using AI by automating key steps: research, comparison, and planning.

First the prompt, then the suitcase

Using AI to plan a trip can feel like a genius shortcut… until the result doesn’t meet expectations. But often the issue isn’t the tool itself, but how you talk to it. To get truly helpful answers, you need a well-crafted prompt.

A structured request helps AI better understand the context and provide relevant, coherent, and personalized results. Be sure to include key elements like:

• Context and Goal. Clarify what you’re looking for (e.g., an itinerary, destination ideas, or comparisons).
• Practical Info. Specify trip length, travel dates, budget, departure city, and number of travelers.
• Personal Preferences. Beach, mountains, or countryside? Europe, Southeast Asia, or elsewhere? Tourist hotspots or off-the-beaten-path? Foodie experiences, cultural visits, or outdoor activities?

You can also define the output format (bullet points, daily itinerary, comparison table) and level of detail (brief summary or in-depth answer). The more precise the prompt, the closer the result will be to your expectations.

Step-by-Step Guide to Trip Planning with ChatGPT

When using a conversational model like ChatGPT for travel or complex, subjective tasks with many variables, it’s important to know that the AI has no preset info about you: responses are based only on what you share in the conversation.

These virtual assistants rely on natural language processing: the model interprets your prompt as a text input and builds the reply using knowledge, inference, and language patterns.

That’s why interactions should be seen as iterative processes, where you gradually add information to guide the AI in generating relevant suggestions.

A general rule for getting quality results is to start with a broad request (e.g., “I want to plan a vacation in Europe in August”), then refine with more specific questions. This creates a progressive, adaptive conversation where the AI sharpens its responses based on prior input.

Our summer holiday will have these parameters:

• Duration: 7 days
• Dates: Between August 10 and 25
• Departure: Milan
• Budget: Max €1,500 per person (flight, hotel, meals, and activities)
• Preferences: Uncrowded beach, local cuisine, light sports (kayak, trekking)

Choosing a Destination with AI

Step one: pick a destination. AI can provide a shortlist of places that meet your criteria, with pros and cons for each.

Prompt Example:
Suggest 3 beach destinations for a 7-day summer holiday departing from Milan between August 10 and 25, with a max budget of €1,500 all-inclusive. Destinations should be uncrowded, have good food, and offer light outdoor activities. List pros and cons.

Result

1. Slovenian Coast (Piran and Portorož)

• Pros: Calm sea, great food, affordable prices
• Cons: Not an “exotic” destination

2. Naxos (Greece)

• Pros: Less touristy beaches, water sports, local gastronomy
• Cons: Requires layover flights, expensive in August

3. Minorca (Spain)

• Pros: Protected nature, quiet coves, local cuisine
• Cons: Car rental almost necessary

Finding Flights and Hotels with AI: Faster Searches

Once the destination is chosen (in this case, Naxos), you can ask the AI to find the best flight and accommodation options. Again, the more specific you are with your criteria, the better the output.

Prompt Example

Find a flight from Milan to Naxos between August 10 and 25 for no more than €350 one-way. Suggest a 3-star hotel with a Booking rating above 8, near the beach, under €100 per night for a double room. Provide at least three options for each, with pros and cons.

Sample Result

• Flight: Milan Malpensa → Athens → Naxos, 2-hour layover. Round trip: €630
• Hotel: Argo Boutique Hotel, ~€95/night, breakfast included, 100m from Agios Georgios beach, great location and reviews

AI might also suggest cheaper options (like a ferry from Athens to Naxos), but the connecting flight was chosen here for convenience.

Note: AI can’t make actual bookings—you must double-check all info on official websites before purchasing.

Day-by-Day Itinerary Planning

A popular AI request is creating custom itineraries that balance rest and activity based on your preferences.

Prompt Example

Create a 7-day itinerary for Naxos with a mix of beach time, light hiking, and local food. Avoid overly touristy places and suggest typical restaurants.

Sample Itinerary (excerpt)

• Day 1: Relax at Agios Prokopios, dinner at To Elliniko
• Day 2: Kayaking at Mikri Vigla, lunch at local kiosk
• Day 3: Hike Mount Zas, dinner in Chalki village
• Day 4: Boat trip to Koufonisia
• Day 5: Visit Apiranthos + Kitron tasting
• Day 6: Snorkeling at Plaka Beach
• Day 7: Stroll through Naxos Town’s old center

The itinerary is flexible and can be adjusted as needed.

Packing with AI: What to Bring

Now it’s time to pack! AI can help you prepare a complete list based on your destination and planned activities.

Prompt Example

Create a packing list for a 7-day trip to Naxos in August with beach, hiking, and kayaking.

Sample Output (excerpt)

• Lightweight hiking shoes
• Water shoes or kayak sandals
• 20–30L hiking backpack
• Sun hat or bandana
• UV-protection sunglasses
• Microfiber beach towel
• Long-sleeve technical shirt (UV/shade use)

What’s Still Up to You?

AI is a great assistant, but it can’t decide if you’d prefer a sea-view room or one closer to the breakfast buffet. Booking, final checks, and personal decisions are still on you.

Some good habits:

• Always read updated reviews from multiple sources.
• Double-check all flight and hotel info before clicking “Book Now.”
• Adjust your itinerary to fit your pace—AI doesn’t know how early you’re willing to wake up for kayaking.

In short: you choose the path, AI helps you map it…and that’s still better than nothing.

A Ready-to-Use Prompt

Now you’ve got all the tools to turn ChatGPT into your personal travel agent. Still unsure how to phrase your prompt? Here’s a plug-and-play formula:

Plan a summer holiday of [number] days departing from [City] between [Dates]. Max budget: [€], covering [all-inclusive/flight+hotel/hotel only…]. Preferences: [beach/mountains/city], activities: [food/sports/culture/relaxation], comfort level: [basic/mid/luxury]. Suggest 3 uncrowded destinations, with flights, accommodation, and a detailed itinerary including restaurants and activities.