I asked ChatGPT to plan my holiday – this is my verdict

As someone unfamiliar with ChatGPT, I was intrigued about how helpful it would be for my travels

Rear view of tourist taking pictures in the old town of Palermo, Sicily, Italy

Francesca ShillcockDigital Travel Editor

August 13, 2025Aug 13, 2025, 11:27 AM GMT+1

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I have a confession to make. I'm not the biggest fan of AI.

Don't get me wrong, I fully appreciate its value in businesses and everyday workflow. And I'm more than aware of the inevitable role it will play in the future of our ever-changing digital landscape. But I wouldn't (consciously) choose to use it in my everyday life.

I've got pals who happily hop onto ChatGPT when they need an email written quickly or are on the hunt for a quick recipe - no judgement here. Meanwhile, in more serious cases, there are reports swirling in the media about using AI for outsourcing things like therapy and counselling.

Maybe it's my lack of experience, and yes, okay, perhaps ignorance, that's making me averse.

And it's not like it's a hot take. Plenty of studies have revealed that although many are excited about AI's future, there are still concerns among the general public.

Two woman explore the back streets of a European city. The woman in the foreground glances over her shoulder and smiles at her friend, who uses her mobile phone to take a video of her surroundings. — Whether planning a city break or sun-soaked trip, using AI could help with your intinerary

But one thing that did intrigue me was using ChatGPT, for example, to plan a holiday. Now we're talking.

It's not just because of my role as Digital Travel Editor that I'm always thinking about my next trip. I'm constantly thinking about where and how I'm going to get to my next dream destination because it genuinely brings me joy.

Part of the fun for me is in the planning, but I was open to the idea of having a solid, foundational itinerary offered to me that I could then tailor to my personal needs and tastes. I knew crucially that it would also save time.

How I used ChatGPT to plan my trip

So how did I use it to plan my trip?

Although I'm not well-versed in speaking to this insightful and reactive little robot, I knew I had to provide it with enough prompts to get the most out of it.

My proposal? A two-night solo city break to Dublin, Ireland, taking place sometime this autumn, with the obvious tourist hotspots included but some hidden gems thrown in, too.

Ireland, Dublin, Temple Bar area, Crown Alley — I asked ChatGPT to plan me a two-night solo trip to Dublin, Ireland, which has been on my travel list for quite some time

Here's what I wrote:

"I want to go to Dublin on a solo trip in the autumn. I want to go for two nights and stay somewhere quite central. I want to see the obvious tourist spots, but I'm also keen to see local gems and hidden, must-see places that won't be full of tourists."

I knew I had to give it enough information to work with, while also trusting the powers that be. This is the result…

ChatGPT's response

I was pleasantly surprised by what Chat provided and how much detail it provided. Here's a quick summary of what it gave me:

"That sounds like an amazing trip — Dublin in autumn has a cosy, vibrant energy with fewer crowds and a golden light over the city. Here's a quick guide to help you plan your two-night solo adventure, with a balance of classic highlights and lesser-known gems."

Trinity College Dublin Campanile, most prominent tourist attractions in Dublin. — Trinity College Dublin, one of the most prominent tourist attractions in Dublin

It then proceeded to give me six detailed paragraphs broken into categories, including: Where to stay (Central, safe and solo-friendly); Recommended solo-friendly places; Must-see tourist spots (the classics); Hidden gems and local secrets; as well as extra tips for solo travellers in Dublin.

It also gave a two-night example itinerary.

Day 1:

Arrive, drop bags
Trinity College → Grafton Street → St. Stephen’s Green
Late lunch at Fumbally
Guinness Storehouse in the late afternoon
Dinner + drinks at The Long Hall or Grogan’s

Day 2:

Kilmainham Gaol tour (morning)
Walk along the Liffey, stop at Chester Beatty Library
Lunch at Brother Hubbard (Capel St)
Explore Smithfield + Collins Barracks Museum
Traditional music at The Cobblestone

Day 3 (Departure):

Easy morning stroll through Iveagh Gardens
Coffee at Shoe Lane
Souvenir shopping (Irish Design Shop / Avoca)

The itinerary was also woven with highlights I definitely didn't want to miss, like walking down Temple Bar (even if just to see it for a few moments before sufficiently running away from the rowdy crowds, stag dos and the like), cute libraries to explore and hidden gardens to wander through.

The grounds of St Patrick's Park, Dublin City, Ireland — I wanted the itinerary to include the obvious attractions as well as hidden gems

Overall verdict: Would I use ChatGPT to plan my holiday?

In short, yes, but in a hybrid way. Using ChatGPT to plan this trip was extremely helpful. Do I need to use it as gospel? No, but it's undoubtedly a great place to start, and the itinerary breakdown is something I'll keep in mind.

However, I believe everyone should take a hybrid approach.

Although it was helpful, I'll still do my own research and ask around those who have been and can personally recommend places.

ChatGPT helped my trip big time, but, for me personally, it won't replace those who have been and can vouch for the best places to eat, see and explore.