As someone who goes on ~15 international trips a year, I am always looking for things to improve how I travel. In the past year or so, AI tools have become a big help. Here’s how I use them.
Planning
I have a “Travel Companion” project set up in ChatGPT. Here are the (unfortunately very pretentious) project instructions, which were themselves AI-generated after I gave a model a bunch of my travel writing).
I’m an extremely well-traveled, discerning traveler (42+ countries with week+ stays) who values authentic, high-quality experiences. When making recommendations:
Food: I have similar tastes to Tyler Cowen – I appreciate ethnic cuisines, hole-in-the-wall gems, and authentic regional specialties that showcase local ingredients and techniques. I want places offering things unique to that destination. Value matters, but I’m willing to pay for genuine quality. Skip generic “good” restaurants – I want what I can’t get in London.
Culture: I’m passionate about art, architecture, and museums, with particular interest in contemporary art and exhibitions that use space creatively. I prefer places with historical context and often want to understand how a place got to be the way it is – its history and economic development. Focus on what’s genuinely world-class or one-of-a-kind in that location.
Travel style: I research thoroughly, book ahead, and appreciate efficient transport. I seek out excellent independent bookshops everywhere. I’m comfortable with both luxury and budget options (though no hostels) and willing to pay for comfort and to save time. I prefer authentic neighborhood experiences over tourist areas.
Unique experiences I value: I’m drawn to unusual, immersive experiences like Dennis Severs House, Musée Mécanique, Rothko Room, or The New York Earth Room – places that are labors of love, demonstrate obsessive dedication to a craft, or offer genuinely transformative spatial experiences you can’t find elsewhere.
Key principle: I’m looking for experiences unique to that place vs London. Don’t recommend good Indian food in NYC or impressive general art museums unless they’re truly world-class or one-of-a-kind – I want what I can’t get at home.
Avoid: Tourist traps, experiences I could have in London, overly commercialized attractions, Instagram-focused spots over substance.
What I value most: Discovering genuinely local and unique experiences, learning something new about a place’s history and development, finding places that demonstrate real expertise, and maximizing the uniqueness of each destination.
This allows me to say “I’m going to X place for a few days, what should I do” and get much better recommendations than the usual not-very-good travel blogs. They’re still not great — I’m sure the prompt could be much better — but they’re a good start. I think the “avoid experiences I could have in London” part is doing a lot of work to filter out stuff that’s good, but not the best use of my limited time in a place.
It’s also fairly useful at directly comparing things — in Mexico City, for instance, I asked it to list all the places with Diego Rivera murals and recommend one that I had to see. Most travel blogs are too completist; it’s helpful to have a filter.
The project’s also useful for dumping in a rough itinerary, asking if it makes sense, and suggesting tweaks. With countries where I’m going to be travelling around a lot, it’s helpful to have it point out that travel between A and C is easier than A and B, for instance.
Before going, or while on the plane, I’ll ask ChatGPT or Claude for detailed-ish history of the place I’m visiting to help me quickly get up to speed. It’s nice to arrive having a bare minimum knowledge of that.
On the trip
ChatGPT Voice Mode has become an indispensable companion in museums with minimal/bad English translations. You can just point your phone at a sign, ask it to translate it, and then it will read you a translation while you look at the object. You can then also ask follow up questions, and generally use it to fill in gaps in your knowledge about the history and context of the objects. It’s as close as it gets to having a private tour guide without actually paying for one. I’ve used this in Indonesia and Mexico so far, and it’s been excellent in both cases, significantly improving my understanding of what I’m seeing. (The only problem is the too-short usage limit.)
The new AirPods Live Translate feature is also very impressive. In Mexico, I was lurking by a Spanish-speaking tour group looking at Diego Rivera murals. I wanted to know what the guide was saying, so I turned on Live Translate, and was instantly hearing a very good quality live translation of her tour. It was very useful! I’m less convinced about the utility of this feature in conversations, but in a presentation context it works very well. I can see myself using it at the theatre or cinema, too.
The Apple Translate app is pretty good, if a little slow. Two other iOS features that are quite useful for communication: after screenshotting something, there’s an option to translate the screen, which is helpful for foreign-language WhatsApp convos (the built-in WhatsApp translation is very glitchy, in my experience). And within WhatsApp or any other app, you can type in English, select the text, hit “Translate” from the format options and then “Replace text with translation”. Very helpful!
Deep Research is also useful when I come across something obscure I can’t quite explain and want to know more about — such as why it took so long for the new highway to be built between Oaxaca and Puerto Escondido. The fact that these models can search local-language news sources and translate/summarize them for me is particularly useful.
What they’re not good for
They’re still not particularly good at telling you what’s happening on a given day in the city you’re visiting, though they’re getting better. (I got a couple of good repertory cinema listings last time I was in the Bay.) They’re also just generally a bit too slow, and relying on good internet is an issue (though increasingly less so, especially if you use an eSIM or have a plan with unlimited 5G roaming, as I do). And their taste isn’t quite there yet, though it’s vastly better than almost any travel blog, publication, or even personal recommendations from (most) people.




