Tools · Solo Travel, Powered By AI
Traveling tech-savvy: using AI as you go
Your smartest travel companion doesn’t need a seat on the plane. From six months across South America down to a blurry pharmacy label in Bolivia — here’s where the practical use cases stop and the slightly ridiculous ones begin.
Ten years ago, half the challenge of solo travel was just finding a Wi-Fi signal. Now the challenge is different — it’s knowing which questions are actually worth asking an AI tool, and which ones you should have just Googled. I use Gemini and ChatGPT constantly, before I leave, while I’m on the road, and after I’m home reminiscing. Some of it is genuinely useful planning infrastructure. Some of it is me photographing a potato in Bolivia because I panicked. Both counts.
Before you go
Building the rough draft
This is the pre-built, obvious use case — but it’s still the one that saves the most time. I don’t ask for a finished itinerary. I ask for a starting point I can then go and fact-check myself.
The brief I give it
Destination, days, budget — I start with the hard constraints first, then let the tool build around them instead of the other way around.
What I actually ask for
Sites, Instagrammable spots, hiking days — a mix of the popular and the personal, so the draft reflects how I actually like to travel, not just a top-ten list.
Where it earns its keep
Pacing — how many days to actually spend in each place before I move on. This is the question I get wrong most often when I plan alone.
The part I don’t skip
Historical context — I ask for the “why” behind a place before I go, so I’m not standing somewhere important reading a plaque for the first time.
The output is never the plan. It’s the first draft of the plan — the thing that makes it comfortable to actually start thinking about a trip instead of staring at a blank map.
On the road
The everyday practical stuff
Once you’re actually moving, AI stops being a planning tool and starts being closer to a fixer. This is where six months through South America actually got easier — money, transport, safety, and food, in real time.
Working out how to actually get there
Buses, vans, ferries, flights — in a new country I don’t know the transport landscape yet. I’d ask what my options were between two points, which companies covered that route, and which one made sense for the day I actually had.
Which neighborhood to actually stay in
Before booking anywhere, I’d ask which areas were considered safer for a woman traveling alone — and in Rio specifically, where it made sense to go out at night versus where to skip, before I ever set foot there.
Finding the top tables, not just the top ten
Asking for the top Michelin-recognized restaurants in a city gets you a much better shortlist than scrolling reviews for an hour — I’d use it as a starting list, then narrow down from there.
Booking the harder-to-find experiences
Working out how to actually book a helicopter tour over Rio isn’t obvious from a search page full of ads — this is where a direct, specific question saved real time.
Navigating Patagonia’s reservation maze
Patagonia runs on a specific set of booking sites and bus companies that aren’t intuitive if you’ve never been. I used it to work out which platforms and which van and bus operators actually made sense for getting between stops.
On the road, part two
The quirky ones
And then there are the questions I never expected to be asking an AI tool — but here we are. These are the moments that make solo travel with a smartphone genuinely feel a little bit like magic.
The nail salon price check, Chile
A completely mundane errand — I wanted to get my nails done and had no idea what a fair local price actually was, so I asked before I walked in.
The pharmacy label I couldn’t read
Standing in a pharmacy with instructions written entirely in Spanish, a language I don’t speak — I photographed the label and asked what it was actually for before I bought it.
“Is this bruise a problem?”
A photo of some unexplained bruising, and a question about whether it called for an over-the-counter fix or an actual doctor’s visit — a genuinely useful first filter when you’re far from home.
The French potato, Bolivia
Sitting in Bolivia, looking at a dish I didn’t recognize, photographing my food just to double-check what I was about to eat was actually what I thought it was.
None of these are glamorous questions. But money, health, and food are exactly the categories where a wrong guess actually costs you something on the road — so they’re also where a second opinion in your pocket matters most.
After you’re home
Turning six months into a memory you can find again
The part of this I didn’t expect to love: I used AI not just to edit what I wrote on the road, but to keep a running record of what I actually did, day by day, for six straight months. Now, when I want to remember a specific stretch of the trip, it’s there to look back through — instead of trying to reconstruct it from memory and a camera roll.
Good to know
Frequently asked questions
Which AI tool do you actually use?
Mainly Gemini and ChatGPT, depending on what I need — Gemini for anything involving a photo (labels, food, injuries), and either one for planning and writing.
Isn’t it risky trusting AI advice while traveling solo, especially for safety or health questions?
I treat it as a first opinion, not a final one — a way to narrow down options or flag when something’s worth taking more seriously, like a pharmacy visit versus a doctor’s visit. It doesn’t replace local knowledge, a real pharmacist, or common sense; it just gets you to the right next question faster.
Do I need to be tech-savvy to do any of this?
No — every example here is just typing a question or uploading a photo into a free app. The skill isn’t technical, it’s knowing what’s worth asking.
Want a rough draft of your trip before you plan it yourself?
I’ll help you build a starting point — budget, pacing, and the questions worth asking before you go.