AI May Know a Lot About Travel, but It Doesn't Know You

Lately it has caught my attention how many people are delegating their vacation to an AI solution. Posts like this one are becoming more and more widespread across social media:

Thoughts on our updated 20 day itinerary for July 2027 with 2 young children:

• July 10th: land in San Jose and stay 2 nights
• July 12th: transfer to Tortuguero for 3 nights
• July 15th: collect hire car in Guapiles and drive to Sarapiqui for 2 nights
• July 17th: drive to La Fortuna and Arenal for 2 nights
• July 19th: drive to Monteverde for 2 nights
• July 21st: drive to Manuel Antonio for 2 nights
• July 23rd: drive to Sierpe, drop off the hire car and catch the ferry to Drake Bay for 5 nights
• July 28th: fly from Drake Bay to San Jose and stay one night
• July 29th: international flight home

The traveler added that they did not want to spend much time on touristy things in La Fortuna or Monteverde, maybe Mistico or a park, and an ATV or zip line once in either location.

I want to be perfectly clear: this is a terrible plan, and the fact that this is becoming a more and more common practice is what drove me to write this piece.

Why a well earned break deserves better

Depending on where we are born, we work between 46 and 50 weeks a year to get some vacation time, and seeing an AI solution butcher that well earned break is beyond what I can deal with.

This proposal starts with 2 days in San Jose. Depending on what you want to discover in Costa Rica, which based on the rest of the trip is nature, adventure and rest, those are 2 days not very well spent. Not to mention that you should actually get to know San Jose to avoid areas that could be considered risky for visitors.

Transferring to Tortuguero is smooth if you have a shuttle service in place, but then moving on to Guapiles, if it is not with another shuttle, you are in for a bad time, because public transportation can be very troublesome.

Then 4 days across La Fortuna and Monteverde when you only want an ATV ride or a zip line, while missing the really good things to do there like the national parks or the hot springs, is missing a great opportunity.

Crossing the country to reach Manuel Antonio and Drake Bay with 2 young kids is not a great idea when there are so many great beach options much closer by. And did the plan consider flights from Liberia, which would make far more sense than doubling back to San Jose? I love Drake Bay and Corcovado, but taking 2 young kids there is a whole different story.

This is about cohesiveness, not intent

This is not a critique of the intent of the plan. All the places in it are amazing. Pretty much all of Costa Rica is. This is a critique of the cohesiveness of the plan.

AI can give you ideas for a trip, but it is never going to understand the experience itself. It is not contemplating the effect of distance on young kids, the state of the roads in rural areas, the reality of public transportation in the country, safety considerations, and so many other elements that seem intangible yet deeply affect the pleasure you get from the trip.

I also want to be perfectly clear that this is not an anti-AI post. AI is great for many things, just not this one. The goal is knowing when to use it, in which cases it shines, and acknowledging when it does not. Human experience is not something we can delegate, and that is one use case AI will never replace.

So, with all of this, just a callout: take care of your vacation experience. Do not delegate it to a very smart solution with no understanding of what it is to be you.

Enjoy your trip. Make it worthwhile.