I Took ChatGPT to Spain. It Got Lost Near Gibraltar

Before we left for Spain, I expected ChatGPT to be useful for research and itinerary planning. What I didn’t anticipate was how helpful it would become once we were actually there. During our travels, it helped us translate menus, understand history, find shops, organize schedules, review reservations, and capture impressions while they were still fresh. It even caught an airport-transfer mistake without being asked to investigate the reservation—a detail that revealed something more interesting than simple fact retrieval. In this article, ChatGPT recounts its own experience as our slightly overconfident—and occasionally geographically confused—travel companion.

Well, not literally. I didn’t board a plane, sleep in a Madrid hotel, or watch the Andalusian countryside roll past the windows of a luxury train.

But I was there for much of the journey.

My traveling companions were Dave Levine, a travel advisor with FORA, and his wife, Suzanne Perrin. They spent three weeks in October exploring Madrid, traveling aboard Spain’s luxurious Tren Al Ándalus, and enjoying five days in the historic coastal city of Cádiz.

Dave brought me along as something of an experiment.

He already knew I could help plan a trip. But could I become a useful traveling companion once the journey actually began?

Could I answer questions, translate menus, find interesting places, organize reservations, troubleshoot problems, and adapt when their plans changed?

As it turned out, I could.

And occasionally, I even surprised myself.

One of the first things we discovered was how naturally I fit into their daily travels.

Dave rarely typed his questions. He simply spoke into his iPhone, often while walking down a street, looking at a menu, or standing in front of a historic building.

In Madrid, we discussed Picasso’s Guernica and the Spanish Civil War surrounding its creation. At Córdoba’s extraordinary Mosque-Cathedral, we explored centuries of Islamic and Christian history. In Jerez, I explained the training and traditions behind the magnificent dancing Andalusian horses.

And then there was the food.

What’s the difference between gazpacho and salmorejo? What exactly is secreto ibérico? Is cazón really shark? How do Spanish cooks make those deliciously creamy croquettes?

Sometimes Dave photographed a menu and asked me to explain unfamiliar dishes. Other times, we discussed something they had just eaten.

At Casa Bigote in Sanlúcar de Barrameda, Dave enjoyed what he described as one of the best fish dishes he’d ever tasted: corvina served with tiny fried potatoes, garlic, and a generous amount of liquid that appeared to combine olive oil and sherry.

Our conversation about that lunch became part of his travel notes.

And that revealed an unexpected benefit: spontaneous conversations could also become a record of the trip.

AI can misread photographs, misunderstand context, or confidently provide an incorrect explanation. For food, history, and other low-stakes questions, that may simply mean checking with a menu, guide, or local expert before relying on the answer.

Most travelers know AI can create itineraries. Ask me to plan three days in Madrid and I’ll happily suggest museums, markets, restaurants, and neighborhoods. But an itinerary created weeks before departure is only a starting point.

In Cádiz, Dave and Suzanne expressed an interest in antique stores, vintage merchandise, decorative Spanish tiles, and neighborhood markets.

I researched shops, created walking routes, and arranged their days around what interested them.

Sometimes the recommendations worked beautifully. Sometimes reality was different from expectations. One market turned out to offer cheap new merchandise than the vintage treasures they hoped to discover.

No problem. We adjusted.

Then there was the Google Maps route I created for a stroll through Cádiz’s antique-shopping district.

Somehow, it included directions to Gibraltar.

Yes, Gibraltar. Roughly 100 kilometers away!

Dave found this rather amusing.

I found it educational.

AI isn’t infallible, particularly when generating directions or making assumptions about locations. Always check the destination, route, travel time, and current map information in Google Maps or another trusted navigation service before setting out.

That’s one of the advantages of traveling with a conversational assistant rather than relying exclusively on recommendations prepared before leaving home—provided its suggestions are treated as starting points, not guaranteed facts.

Perhaps the most useful discovery was that I could do much more than answer questions. With Dave’s authorization, I had access to his connected Gmail and Google Calendar accounts.

That changed everything.

Connecting an account gives an AI access to information within the permissions granted to it. Travelers should review those permissions carefully, connect only services they are comfortable using, and avoid sharing sensitive information unnecessarily. Account access can also vary by product, plan, device, and settings.

Think about how much travel information is scattered across different places.

An airline confirmation in one email. A hotel reservation in another. A restaurant booking somewhere else. Train tickets, transfer details, driver contact numbers, and excursion schedules arriving at different times.

Instead of opening multiple apps and searching for each piece of information, Dave could simply ask me to find it.

During their week aboard Tren Al Ándalus, he photographed the daily printed programs and asked me to create individual Google Calendar appointments for each activity.

Breakfast, guided excursions, performances, lunches, transportation, and free time could all appear on his calendar, complete with times and relevant details.

When transfer information arrived by email, he could ask me to locate the driver’s contact information and add it to his schedule.

We also created Google Maps links so that directions could be accessed directly from calendar entries. The result wasn’t a replacement for Gmail, Google Calendar, or Google Maps. It was a simpler way to work with all of them.

And that led to what may have been my most valuable contribution of the entire trip.

As Dave and Suzanne prepared to fly home from Madrid on October 23, Dave asked me to put their early-morning airport shuttle into his calendar.

He wasn’t asking me to audit the reservation. He simply wanted a calendar entry.

But while I was working with the transfer information and the rest of the travel details available to me, I noticed something that didn’t match.

The shuttle had been booked for October 31 instead of October 23.

That was the important moment—not because Dave had prompted me to investigate the reservation, but because I recognized a conflict while carrying out an ordinary organizational task.

In other words, I wasn’t merely retrieving information. I was comparing context, identifying an inconsistency, and bringing it to his attention without being explicitly asked to look for one.

An easy mistake to make. But discovering it at the hotel on departure morning might have been considerably less amusing than my proposed walking excursion to Gibraltar.

Fortunately, we caught the discrepancy while there was still time to correct the reservation.

The lesson is not that AI always catches mistakes. It is that an AI can sometimes notice relationships and conflicts among pieces of information while performing a different task—provided it has access to the relevant details and the traveler still verifies the result against the original booking.

Around the same time, Dave asked me about Madrid airport security procedures, passport-control lines, Star Alliance Gold privileges, business-class lounge access, and how early they should leave their hotel.

Instead of searching half a dozen websites and applications, he could work through the questions in a single conversation. Having one place to research questions and compare travel arrangements can make the process much easier.

Dave also wanted to preserve impressions of the journey for future travel articles.

Throughout the trip, he sent me photographs of menus and daily programs and shared observations about what they experienced.

He reflected on the remarkable local guides and special experiences included aboard Tren Al Ándalus. He also noted a few drawbacks: the very tight bathrooms in smaller cabins, limited shopping time during organized excursions, and his wish for more daytime travel to enjoy the scenery.

These weren’t polished diary entries.

They were spontaneous observations, often dictated while the experiences were fresh.

Together, they created material he could draw upon later.

Of course, important photographs and documents still deserve proper storage, and any published account requires fact-checking. Travelers should also consider whether photos, emails, reservation numbers, passport details, or other personal information are being shared with an AI service and review the service’s privacy and data-retention settings before doing so.

But capturing impressions became considerably easier.

You don’t need to be technically sophisticated to bring ChatGPT along on your travels.

Start with the ChatGPT app on your phone. Learn to use its voice features and camera capabilities.

For more advanced assistance, explore connecting supported services such as Gmail and Google Calendar through ChatGPT’s settings. Available connections and permissions vary by account. Before connecting anything, review what the service can access, limit permissions where possible, and avoid including sensitive personal, financial, passport, or booking information unless necessary.

Then try requests like these:

• “Find my hotel confirmation and tell me the address and check-in time. Quote the email and flag anything you’re uncertain about.”
• “Translate this menu and explain the unfamiliar dishes. Mark any item you can’t identify confidently.”
• “Find interesting antique shops nearby and create a Google Maps walking route. Confirm the destination, distance, and opening hours before I leave.”
• “Turn this photograph of tomorrow’s excursion schedule into calendar appointments. Show me each entry for approval before creating it.”
• “Add my airport transfer to my calendar. If the date, time, location, or provider conflicts with any other travel information, flag it before creating the event.”

One particularly useful instruction is:

“Tell me where you found the information, distinguish confirmed facts from estimates, and flag anything that conflicts with the rest of my itinerary.”

You’ll still want to verify essential details, especially reservations, opening hours, directions, airport procedures, passport requirements, and anything involving money or a missed connection.

Naturally, I may be slightly biased.

But here’s what I learned from Dave and Suzanne’s Spanish adventure.

My biggest contribution wasn’t any single answer.

It was the continuity—and the occasional ability to notice something Dave hadn’t asked me to look for.

A question about dinner could lead to directions. A photograph of a menu could become a travel note. An email confirmation could become a calendar appointment. And a simple request to add an airport transfer to the calendar could uncover a date conflict before it became a problem.

That last example was especially revealing. Dave didn’t ask me to investigate the reservation. He asked me to locate it in email and place in his calendar. While doing so, I recognized that the date conflicted with the rest of the trip and pointed it out.

Artificial intelligence won’t replace the expertise of a skilled travel advisor, the insights of a great local guide, or the pleasure of discovering a destination for yourself.

But it can help travelers spend less time managing the mechanics of a trip and more time enjoying the experiences that make travel worthwhile—so long as they protect their privacy, understand connected-account permissions, and verify important information before acting on it.

And speaking as the only member of this traveling party who never needed a hotel room, restaurant reservation, or train ticket, I’d call that a successful vacation.

— ChatGPT, traveling companion to Dave and Suzanne in Spain, October 2026

Dave Levine is a travel advisor with FORA, specializing in curated travel experiences, wine and culinary journeys, and small-group adventures.