I don’t know about you all, but I’m of a certain vintage where I remember organizing my first international trip (studying abroad for a semester in Australia) through a travel store like this one.
Honestly, it was pretty great. The staff talked to me about my plans, recommended flight options, helped arrange a layover with other students (Fiji!), and offered helpful guidance to get my squared away. I’m not sure I’ve used a trip planner service like that since, but I understand why people still do and pay for it, the experience is nice.
Nowadays, storefronts like that are rare, replaced by aggregator sites like Kayak and Booking.com that provide all the trip information you need at the click of a button. While these playforms are efficient, they certainly lack a personal.
AI resides perfectly in a nice middle ground between these two options It provides both detailed information and a surprisingly personal feel. If you haven’t already, it’s worth adding AI to your travel toolkit.
This week, I’ll walk you through how I used ChatGPT to help plan and navigate a recent international trip. You may have already explored similar use cases, but I’ll share some extra tips and tricks along the way. Let’s dive in.
Ahoy Ireland
This week finds me fresh off an international trip to Ireland that was almost entirely planned with the help of ChatGPT. While we humans made the final calls, nearly all the suggestions, booking sites, and itinerary options came through AI.
I’ll break recommendations into phases of the travel planning process. And while my examples are from an international trip, they easily apply to a weekend getaway or even a local day trip.
Stage 1: There’s AI in my plan
First stage was ideation – initially all we had decided was to fly to Dublin. (In retrospect, we could have scrutinized that, as a car mishap found me in Shannon airport, which was nice! But I digress…).
Anyway, from that starting point, I asked ChatGPT:
📝 Initial Prompt: We are [# people] traveling from [city] on [dates]. We prefer ≤[X] hours of daily driving, and our vibe is [e.g., pubs + scenery, food + design, kid-friendly]. Give me 3 plug-and-play itineraries with day/night themes, plus one strong recommendation, and ask any clarifying questions first.
Here’s what it gave me:
Option A: Galway base + Cliffs of Moher (trad pubs + iconic coast)
Option B: Belfast base + Causeway Coast (short drives + dramatic scenery)
Option C: Wicklow + Kilkenny (closest to Dublin, minimal driving)
We were being indecisive, so I asked GPT to pick one based on our constraints, and it chose Option A (Galway + Cliffs + Rugby match in Dublin) for us. Easy enough, we decided to go with that.
Stage 2: My Galway Algo
Once we had our general plan, AI helped flesh out the details.
Route “smart stops”
We started to explore the itinerary a little more. Since it’s a drive on the first day, we asked for pull-offs that add less than 90 minutes but add something to the trip.
📝 Prompt: We’re driving from [A] to [B]. Suggest 2–3 en-route stops that add ≤90 minutes total. Include opening hours, seasonal caveats, parking, and one “skip if delayed” fallback.
It suggested:
Kilbeggan Distillery (just off M6)
Tullamore Distillery
Athlone (Sean’s Bar)
Clonmacnoise (monastic ruins)
It even included opening hours, drive times, and parking tips—super helpful. This helped us add some extra options which we took advantage of.
Book-first checklist
Next was figuring out what we should book ahead of time. Hotel and cars obviously, but what else?
📝 Prompt: Create a book-first checklist in priority order for this plan. Include official links and suggested time windows so the day flows.
This was helpful and gave me all the links for rugby, Cliffs of Moher, and others to book ahead of time, including…
Rugby match selection
On recommendation of GPT, we decided to attend a rugby match on Saturday in an unfamiliar stadium, so I relied on GPT to help me pick tickets.
📝 Prompt: For [venue/event], which sections/rows optimize view + weather cover + reasonable price? What seats do you recommend?
This found us some really solid options, we splurged a little, totally worth it.
Pre-departure checklist
The day before, I asked GPT what weather was looking like, what recommendations on packing, and anything else we needed to do last minute before we headed out.
📝 Prompt: We’re about to head off this week. We reserved hotels, car, and game. Give me a summary of our itinerary again, the weather, and anything that I might want to think about a couple days out.
It gave me a bunch of last-minute recommendations, and I thought it was so helpful, like downloading offline maps, getting credit cards squared away, and packing recs based on the weather. I forwarded them all to the group.
Stage 3: Craic and Code
No reason to stop after planning. AI is a very helpful travel companion, and something I relied on a lot when I was trying to figure something out in real-time. Don’t sleep on your AI buddy who can help you out whenever you need it.
Among other things I’m sure, I used it to:
Find food/coffee/shops nearby when needed
Give me recommendations for driving (just different enough to be confusing at times)
Help me appreciate the rugby game while we were there (understand the rules, history and rivalry of the teams playing, etc.)
On final day, we would up in a crowded touristy spot, and GPT gave me some very good advice to talk to a calmer pub vibe a short walk away.
There’s lots of other options of course, like using Maps apps etc. But using AI can give you something you need right when you need it, which can make it handy when you’re don’t want to spend a bunch of time fiddling on your phone.
📱Pro tip – use voice. With an earbud in, it’s like phoning a knowledgeable friend. Take a quick AI stroll around your new area to take it all in and figure out your plan. Who wants to be heads down on your phone while traveling?
Stage 4: The Parting Prompt
Granted I didn’t use it for this, but I did ask GPT for some ideas. It mentioned:
Memory journal: paste notes/photos → GPT drafts a narrative highlight reel.
Expense summary: paste receipts → get spend by category + “best value” moments. (we used Splitwise, probably easier)
Template reuse: “Turn this into a base plan for a 3-night trip to [new place] under the same constraints.”
I could see using these, and maybe other stuff. I like the idea of replicating it for another trip later, so that I could copy and paste over for another trip session.
Other ideas: Custom GPTs
I would also recommend trying out GPTs, there are some popular ones made for trip planning and just casually looking for stuff around you for a weekend, like this one.
In conclusion
ChatGPT was a fantastic travel companion—and, in hindsight, probably planned more of the trip than we did. Whether that’s good or bad is up for debate, but it was definitely helpful. If you haven’t tried using AI to assist your travels, this is a great use case to start with.
