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How I planned my vacation using ChatGPT



Planning your vacation abroad is not a simple task when you do it on your own. It's easy when you go through a travel agent but it's always much more cheaper if you do it yourself. This time I decided to do it on my own. However it's a hassle and much more research as always, but this time I had ChatGPT for help. Which made my entire trip planning much more convenient. 

Destination

First thing's first. I created a project in ChatGPT for my vacation 2026 and opened chat. I provided my requirements.

  • Per person budget that I'm willing to spend
  • Dates of travel
  • With whom I'm traveling. My family in this case.
  • What we like to do and what we don't like to do
  • Our meal preferences
  • Shopping expectations
  • Must included and optional things
  • A list of my personal preferred destinations
With this information ChatGPT gave me a few options.

1. Malaysia
2. Thailand
3. Singapore + Malaysia

With some back and forth discussions with the family and shuffling designations we decided on Thailand considering the budget, as it checks all of our boxes including budget shopping, beach vacation, activities and food. 

Itinerary

Then the next step was the finalize the itinerary. For this we gave few things that we'd like to do and things we don't like to do.

Likes:

Nature, Shopping, Beach, Photography, Architecture, Culture.

Don't likes:

Night clubs, Red streets, Boxing, Captured animals etc.

This gave us a few itineraries which then we finalized to Phuket and Bangkok.

Flight Tickets

ChatGPT has an option to find cheaper flight tickets and notify whenever there's a cheaper option available for the given dates. It's a great feature but for some reason cheaper ticket prices never received. I had to manually check prices from various flight booking websites to find the cheapest option. I found that Mondays and Tuesdays were the cheapest in the month of August so we went with that. However kept the alert on for cheaper prices with ChatGPT just in case.   

Hotel Booking

I did this in two steps. 

First step is to find out the general area stay in which would be convinient for us to reach for multiple attractions and has a nice view. Can walk to most places with 10-15 mins which would cut our taxi fair significantly.

Surprisingly ChatGPT has a good sense locations when it comes to finalizing this general area.

However I'd ask a second opinion from Google Map's AI feature to double check this so you'd get real time data from the map itself.

Then the second step is to finding the hotel.

You could install Booking.com plugin to ChatGPT and then directly access their hotels based on your prompt.



 Make sure to provide these requirements for the prompt.

  • Budget range
  • Star rating requirements
  • Consider recent customer reviews
  • Meal requirements - We took with breakfast
  • Location & conveniences to travel. i.e. closer to a market, or closer to an attraction, closer to a beach etc.
This may spit out a few hotels and it's up to you to check reviews and do your usual background checks before booking. 

Before you book your hotel, make sure to see your premises in google maps and in street view. One mistake I did was booking without checking it out in Google maps and ended up booking a hotel in an alley where a taxi can't reach directly. So, had to carry our bags few yards.

High level itinerary

Now the Hotels are booked and the destinations are finalized, we have to plan for each day. Make sure to keep everything documented in either a google doc or something like Outline. Make sure to provide exact flight times as well so ChatGPT can take them as well into account. 

Make sure to consider hotel checking-checkout times as well when you plan this.

First plan a high level full trip itinerary which will include the days and activities including where you'd spend the night. Also include any travels like flights, train etc.

Travel Route

Once we have the high level itinerary, next step is to plan the travel route. 
For this we may need the Google Maps help again as ChatGPT is not the best with roads and locations as of now.

You could plan the route with Google maps and then share that route details with ChatGPT so it can include that to the document.

Detailed itinerary

Then the next step is planning for each day one by one. Make sure to connect ChatGPT with a document like Google docs so it can have a seamless access. Otherwise it'll tend to forget what you planned previously.

Once This is done you should have a detailed itinerary for the whole trip. 

Make sure to ask ChatGPT to check for any issues in this plan once it's done so it can proof read this plan.

Weather Forecast & Alternatives

Before like two weeks or so make sure to ask ChatGPT to check the weather forecast in your destinations and make recommendations for alternatives in case of weather disruptions etc. For example, if you have planned any boat rides, it could get cancelled due to rain, or some theme park rides could cancel due to weather etc. With this alternative planning it won't be a surprise when you get there.

Final Checklist

ChatGPT would conveniently generate a checklist for documentations including travel documents, phone chargers and packing essentials and even stuff like currency. This is a great exhaustive list that could make your travel easier. 



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