7 things I learned using ChatGPT to plan my vacation
Once seen as futuristic pipedreams, ChatGPT and other AI programs are swiftly becoming integral to our lives. But do these tools really work, and can we trust them with something as intricate as a travel itinerary?
To put this to the test, I recently challenged ChatGPT to plan my entire city break to Lisbon. You can read about the trip here, but needless to say, the results of the AI-powered adventure were a mixed bag.
ChatGPT easily grasped some aspects of trip planning but fell flat in many other areas. This ultimately made the trip way more stressful than I’d anticipated.
Related: 9 awesome features you might not know about Google Flights
If you’re reading this, you're probably considering using ChatGPT to plot your own vacation. Here are some things I learned, so you won't make the mistakes I made.
Remember, this is still new technology
Despite the hype, ChatGPT is not an all-knowing cyber lifeform. Sure, its responses can seem eerily humanlike, but the tool is in its infancy. Like any infant, it is still learning about the world and how to interact.
Broadly speaking, ChatGPT answers our questions by drawing upon available information (Google reviews, certain third-party website data and more). It then uses a form of language processing to predict how its answers should be framed based on its previous experience with similar prompts.
This poses a few problems when using ChatGPT to plan your travel. It just doesn’t know enough about the world yet. If its source material is scarce or prior "life" experience is menial, any recommendations it gives will fundamentally reflect that — and they do.
ChatGPT isn’t a travel super guru, even if it sometimes sounds like one. Think of ChatGPT as a rough travel guide, but don't expect it to know everything.

The bot is desperate to please and will lie
ChatGPT wants to keep you happy. This meant that when I asked for things to do in Lisbon, it would always give me an answer, even if it didn’t have one.
For example, I’m a huge magic fan, and when I visit a new place, I often try to catch a show by a local performer. As such, I asked ChatGPT for its best recommendations to see magic in Lisbon.
“In Lisbon, one of the best places to witness magic performances is at the Magic Palace. The Magic Palace, also known as Palácio do Mago, is a renowned venue for magic shows and illusions,” the bot enthused. “Located in the heart of Lisbon, this intimate theater offers a captivating and immersive experience where talented magicians showcase their skills and leave the audience in awe.”
This ticked all my boxes. However, when I pushed for more information, ChatGPT said: “The information I provided about the Magic Palace was purely fictional and not based on any real place or event.”

At other points, it sent me to food markets that didn't seem to exist because it knew I wanted specific street food recommendations.
ChatGPT will tell you exactly what it thinks you want to hear rather than say it doesn’t know something.
Double-check everything
Since ChatGPT can bend the truth, it goes without saying that you should exert caution if it's planning your vacation. It’s not just outright fabrications that could derail your trip; there are also minor (but crucial) inaccuracies.
ChatGPT recommended a genuine restaurant that was apparently famous for a specific local dish. When I arrived, the place didn’t serve the dish and never had. While small, these errors stack up and could be extremely problematic in other scenarios — like if I’d asked for a kid- or vegan-friendly restaurant.

The later versions of ChatGPT can access the internet for information; this causes more room for potential error, given that the internet is notoriously rife with misinformation.
Think of ChatGPT as you would any other search engine and keep your wits about you. If something on your itinerary seems fishy, it's probably because it is.

It will send you to busy tourist spots
When ChatGPT recommended real places to visit, it didn’t fare too badly. However, these places were often the most popular tourist spots.
This isn’t necessarily a bad thing. If a place is busy, it’s usually because it’s good. However, it meant that I spent a lot of time waiting in line. I’m not against waiting for a great experience, but it gets annoying if you have to do it at every stop.
The issue is that ChatGPT seems to draw heavily on third-party listicles and Google reviews. I realized afterward that many of ChatGPT's recommendations appeared in the top articles on Google after searching “best things to do in Lisbon.” These are the same recommendations most other people are also finding, so expect high footfall.

I don't blame the bot for sending me to popular places, but it’d be nice if it diverted more from the well-worn track.
If you’re happy only visiting touristy spots throughout your vacation, this won’t be a problem. Some of the tourist sights are very good. If you’re looking for more authentic hidden gems away from the crowds, ChatGPT isn’t the guide for you.
Your itinerary could become an expedition
ChatGPT does not understand the human concept of a relaxing travel experience — soaking up the surroundings of a new place, immersing yourself in its culture and enjoying yourself. Often it struggled to put together a list of activities close enough to avoid incredibly long walks or Uber rides to the far sides of town between activities.
The order of its itinerary was illogical. It would suggest visiting a historical attraction, then eating lunch somewhere that was a 20- to 30-minute cab ride away. Then, it would send me back in the other direction via another marathon Uber journey.
It doesn’t appreciate that you might want to enjoy each destination before darting to the next.
You might be fine with this, but I found it frustrating. It meant I was more focused on rushing from point A to point B than enjoying the city I was in.

Don’t forget to interact with real people
Don't overlook real human conversations if you use ChatGPT as your tour guide. When conversing with a chatty AI, it’s easy to get swept up and do only that — especially when traveling solo.
The best parts of my trip were when I chatted with locals or other tourists and followed their recommendations instead of the bot's. Humans understand other humans way better than ChatGPT can. In my experience, real human advice is always more enjoyable.
It sounds cheesy but talk to people. You never know who you’ll meet and what adventures they may set you on.
Ways ChatGPT could help you plan a vacation
Reading all this might sound like enlisting ChatGPT as a travel planner is a wasted endeavor, but it can still be useful.
The trick is to only use it as a broad guide that gives you the margins of a plan and allows you to complete the rest. If you have no idea what the main sights are at your destination or where the best bars are, ask ChatGPT. It'll quickly provide you with a shortlist of potential options. Then all you need to do is check them online to see if they fit your brief.
Likewise, if you're unsure about the budget, I found ChatGPT fairly accurate in giving a ballpark figure of expected daily costs. It was also helpful in choosing the destination based on the period I wanted to travel; it also successfully created a checklist of what to pack and the most efficient ways to get from point A to point B. The key is to use it in moderation when you hit a block, need some inspiration for your trip or want help with logistics.
Bottom line
If you use ChatGPT to plan your vacation, be specific about your location. Cities are big places, and the bot doesn’t understand convenience or distance.
Ask for a broad travel guide rather than a set plan. ChatGPT can provide many helpful suggestions, but don’t let it make the final decision for you. If it sounds fun, do it. If it sounds boring or inconvenient, don’t.
Double-check any itinerary items it suggests. ChatGPT will get things wrong — a lot. Your due diligence will save you a lot of time once you’re on the ground.
If you're in doubt, ask a local or a fellow traveler for their recommendations.
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- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
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Rewards Rate
| 4X | Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year. |
| 4X | Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year. |
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You may be eligible for as high as 100,000 Membership Rewards® Points after spending $6,000 in eligible purchases on your new Card in your first 6 months of Membership. Welcome offers vary and you may not be eligible for an offer.As High As 100,000 points. Find Out Your Offer.Annual Fee
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Why We Chose It
There’s a lot to love about the Amex Gold. It’s a fan favorite thanks to its fantastic bonus-earning rates at restaurants worldwide and at U.S. supermarkets. If you’re hitting the skies soon, you’ll also earn bonus Membership Rewards points on travel. Paired with up to $120 in Uber Cash annually (for U.S. Uber rides or Uber Eats orders, card must be added to Uber app and you can redeem with any Amex card), up to $120 in annual dining statement credits to be used with eligible partners, an up to $84 Dunkin’ credit each year at U.S. Dunkin Donuts and an up to $100 Resy credit annually, there’s no reason that foodies shouldn’t add the Amex Gold to their wallet. These benefits alone are worth more than $400, which offsets the $325 annual fee on the Amex Gold card. Enrollment is required for select benefits. (Partner offer)Pros
- 4 points per dollar spent on dining at restaurants worldwide and U.S. supermarkets (on the first $50,000 in purchases per calendar year; then 1 point per dollar spent thereafter and $25,000 in purchases per calendar year; then 1 point per dollar spent thereafter, respectively)
- 3 points per dollar spent on flights booked directly with the airline or with amextravel.com
- Packed with credits foodies will enjoy
- Solid welcome bonus
Cons
- Not as useful for those living outside the U.S.
- Some may have trouble using Uber and other dining credits
- You may be eligible for as high as 100,000 Membership Rewards® Points after you spend $6,000 in eligible purchases on your new Card in your first 6 months of Card Membership. Welcome offers vary and you may not be eligible for an offer. Apply to know if you’re approved and find out your exact welcome offer amount – all with no credit score impact. If you’re approved and choose to accept the Card, your score may be impacted.
- Earn 4X Membership Rewards® points per dollar spent on purchases at restaurants worldwide, on up to $50,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 4X Membership Rewards® points per dollar spent at US supermarkets, on up to $25,000 in purchases per calendar year, then 1X points for the rest of the year.
- Earn 3X Membership Rewards® points per dollar spent on flights booked directly with airlines or on AmexTravel.com.
- Earn 2X Membership Rewards® points per dollar spent on prepaid hotels and other eligible purchases booked on AmexTravel.com.
- Earn 1X Membership Rewards® point per dollar spent on all other eligible purchases.
- $120 Uber Cash on Gold: Add your Gold Card to your Uber account and get $10 in Uber Cash each month to use on orders and rides in the U.S. when you select an American Express Card for your transaction. That’s up to $120 Uber Cash annually. Plus, after using your Uber Cash, use your Card to earn 4X Membership Rewards® points for Uber Eats purchases made with restaurants or U.S. supermarkets. Point caps and terms apply.
- $84 Dunkin' Credit: With the $84 Dunkin' Credit, you can earn up to $7 in monthly statement credits after you enroll and pay with the American Express® Gold Card at U.S. Dunkin' locations. Enrollment is required to receive this benefit.
- $100 Resy Credit: Get up to $100 in statement credits each calendar year after you pay with the American Express® Gold Card to dine at U.S. Resy restaurants or make other eligible Resy purchases. That's up to $50 in statement credits semi-annually. Enrollment required.
- $120 Dining Credit: Satisfy your cravings, sweet or savory, with the $120 Dining Credit. Earn up to $10 in statement credits monthly when you pay with the American Express® Gold Card at Grubhub, The Cheesecake Factory, Goldbelly, Wine.com, and Five Guys. Enrollment required.
- Explore over 1,000 upscale hotels worldwide with The Hotel Collection and receive a $100 credit towards eligible charges* with every booking of two nights or more through AmexTravel.com. *Eligible charges vary by property.
- No Foreign Transaction Fees.
- Annual Fee is $325.
- Terms Apply.

