Using AI for Travel Planning
We’ve had a quieter few months lately and I have been using it to do a lot of travel planning. In Playa del Carmen we didn’t have a lot to do on a day to day basis and here in London we’ve had a lot of rainy cool days. In the next twelve months we’re going to several places that are new to us and that require pretty in depth research and planning to make sure we maximize our time. As such, I’ve been utilizing both ChatGPT and Google Gemini extensively. If you’re new to using AI, it can be a great tool for research and ideas. Here’s how I’ve been using it and some tips and tricks.
Deciding Where to Go
Next year we’ll be in New Zealand for 9 weeks. I was overwhelmed figuring out where to go, how long to stay, and how to get around. Short of buying guide books I wasn’t sure where to start.
I started with basic google searches like “4 weeks on the South Island of New Zealand”. The challenge with Google searches is that it is only going to bring back web pages that are associated with those key words. Then I had to click through every link to see if the content was relevant. And let’s be honest, not many people have blogs where the title is “4 weeks on the South Island of New Zealand”!. Most of the search results were packaged tours. And that’s not the kind of experience we are after.
This is where AI really helps me. I turned to my trusty pal, ChatGPT and entered the prompt:
Notice how in AI I can put in a full conversational paragraph. Because of my chat history, ChatGPT already knows we’re nomads. It knows that we’re not fancy people. It knows that we’re not backpackers. I don’t have to repeat this in every prompt. (Scary? Maybe, but also very helpful!). I can also go back to previous searches and pick up where I left off months later. This is a huge benefit of using AI.
ChatGPT came back with some questions for me: Do you want to fly out or ferry out? That makes a big difference in the route. Do you want to pick up and drop off the car in the same location? Or pay an additional fee for a drop in a difference city? It then gave me a few options based on the questions above.
Once I thought the picture was becoming more clear in my mind, I did a comparison with Google Gemini. The neat feature of Gemini is that it incorporates Google Maps and plotted the stays onto a map that I could visually look at. The route was not right.
The itinerary I thought was good (based on my prompt of 4 stays) made for too long of driving days. So I went back and said: what if we do x,y,z instead? And it made an adjustment. So I tweaked again. I asked more pointed questions. I asked about the weather. And finally, I feel good about our high level plan. This high level plan allows us to book our accommodations, which is typically the first thing I’ll secure for a destination. We’re now at 7 weeks on the South Island, with 4 week long stays and 6 shorter stays in between.
Detailed Itinerary Planning
I’ve also used Google Gemini and ChatGPT extensively for shorter stays in Spring/Summer 2026 to map out detailed itineraries. We head to Istanbul in early March. Istanbul is a massive city (16 million residents) that spans 2 continents. There are centuries of history to explore, incredible food to eat, and a new culture to experience. How do we figure out what to do for 21 days? Enter AI.
Here was my prompt: (note, AI doesn’t judge you for poor spelling or lack of grammar!)
“we'll be in istanbul for 3 weeks. we're staying in the Beyoğlu neighborhood. we'd like to explore both the european side and the asian side. we'll do 1 tour, but the rest we'd like to maximize free sites and walking. we will eat out lunch, low to moderate prices in restaurants. put together an itinerary, focused on walking and public transportation to see the historical sites.”
The result? A day by day itinerary of where to go and what to do. Anything I wasn’t interested in I asked it to remove and regenerate the list. I later tweaked this prompt to include actual dates and restaurant recommendations. I asked about transportation options. I asked it to put the list in a format that I could easily export into Google Sheets.
Here’s an example though of a mistake that ChatGPT made! March 8, 2026 happens to be a Sunday, not a Saturday. I’m not sure what year it thought I was referencing, but it’s not 2026! When I pointed it out, ChatGPT said “Oops, my bad!”.
Once I had my general itinerary, I then continued to research things such as: where to find ATMs at the airport, what time were prayer services at the mosques, what to expect since we’ll be there during Ramadan, and if we needed to buy passes for the Blue Mosque, the Hagia Sophia, and the Basilica Cistern in advance (the answer was yes!)
While we won’t follow the exact itinerary day by day, this gives us a guide of things to do in whatever city we’ll be in. I used this same approach for Rome, Florence, and Bologna where we have shorter stays and want to see it all!
Tips and Tricks That Work For Me
I use free versions of ChatGPT and Google Gemini. I haven’t felt the need to buy a paid version. Sometimes I hit my search limit for a day on ChatGPT 5, and it regresses back to version 4. No big deal.
Be specific in your prompts.
I still use general Google Searches when looking for tours, ticket sites, etc. Often if I ask for URLs from AI it doesn’t give me the official sites that I’m looking for.
Keep your eyes open for hallucinations (mistakes). It isn’t perfect and shouldn’t replace using your own logic and intuition. I’ve had it make mistakes on dates and return information I wasn’t asking for. It is a start, but not foolproof.
Don’t put sensitive information in that you wouldn’t want a bad guy to know. It is still the internet!
Someone asked me recently if I was concerned that ChatGPT wasn’t using live, real time data. From my perspective that doesn’t matter. Maybe the restaurant it recommends is no longer open. Or there is a hot new restaurant that opened yesterday that it didn’t know about. We use this as one of many sources of information. But it is a fantastic way to start.
Whether you are planning 9 weeks in New Zealand or 4 days in Florence, using AI is an incredible way to enrich your travel planning. It can provide a baseline of itineraries and help you be prepared to enter a new culture. We highly recommend it!