How I Plan a Trip With AI in 48 Hours

Not long ago, planning a solo trip from scratch took the better part of a week. Destination research, flight options, hotel shortlisting, itinerary building, packing lists — each piece demanded its own time and its own browser tab spiral. These days, I can pull together a solid, personalized trip plan in about 48 hours. Sometimes less. The difference is that I’ve learned to use AI tools the right way, which means knowing what to hand off and what to keep for myself.

Here is my step-by-step guide to help you plan a trip with AI in record time.

The first 30 minutes: framing the trip

I don’t start by Googling anything. I start by talking to Claude.

I give it the basics — where I’m thinking of going, roughly how long, what kind of trip I want (active, cultural, slow travel, a mix), and any constraints like budget range or mobility considerations. Then I ask it to push back on me. What am I not thinking about? What’s the best time of year to go? Is there somewhere nearby I might like even better?

This conversation does something a search engine can’t: it helps me sharpen what I actually want before I start building the plan. Solo travel at 50-plus is different from travel at 30. You know what you don’t like. You have standards. Getting clear on those upfront saves a lot of backtracking later.

Research without the rabbit hole

Once I’ve landed on a destination, I switch to Google Gemini for research. I use Gemini specifically here because of its integration with Google Search — it pulls current, cited information rather than working purely from training data. That matters when I’m asking about visa requirements, current entry policies, or what’s actually open in a city right now.

I ask broad questions first: what are the neighborhoods worth knowing, what’s the general lay of the land, what do first-time solo visitors typically miss or get wrong. Then I get more specific — day trip options, transit logistics, whether a rental car makes sense or if the city is walkable enough to skip it.

I’m not looking for a finished itinerary at this stage; I’m building the context needed to plan a trip effectively with AI. The more I understand a destination before I start making decisions, the better every subsequent decision gets.

Building the actual itinerary

This is where I come back to Claude. I’ll feed it everything I’ve gathered — the destination, my travel dates, the neighborhoods I want to base myself in, the experiences I’m prioritizing, and anything I’ve already committed to (a restaurant reservation, a tour I’ve pre-booked, a rest day I know I’ll need).

Then I ask it to build a day-by-day framework. Not a minute-by-minute schedule — a framework. I want to know what’s geographically sensible to group together, which days should be heavier and which lighter, and where I have flexibility to improvise.

The output isn’t a finished plan, but a flexible draft. When you plan a trip with AI, the tool does the structural heavy lifting while you handle the creative editorial work. That division is what makes it efficient.

The logistics pass

Once the itinerary skeleton is in place, I do a logistics pass — and this is often where solo travelers lose hours they don’t need to lose. I ask Claude to flag anything in my plan that requires advance booking, anything with limited operating hours or seasonal closures, and any transit connections that might be trickier than they look on paper.

Again, I verify anything time-sensitive with Gemini or a direct source. AI tools are not infallible with current operational details, and I’ve learned to treat logistics information as a starting point, not a final answer. But having the AI surface the questions I need to verify is itself a time-saver.

Packing and pre-departure

By the end of day one, I usually have a working itinerary, a shortlist of accommodations, and a clear picture of what I still need to confirm or book. Day two is for finalizing bookings, building my packing list, and doing any last-minute research on specific restaurants, museums, or experiences I want to prioritize.

For packing, I give Claude my destination, the time of year, the length of the trip, and my planned activities. It generates a list I then cut down to what I actually need. Traveling solo means you carry everything yourself, so packing light isn’t a preference — it’s a discipline.

What AI can’t do

I want to be honest about the limits here, because the hype around AI travel planning tends to oversell it.

AI tools don’t know your body. They don’t know that you need a slow morning before a big walking day, or that you’ll regret booking back-to-back museums. They don’t know that you’ve been to Rome three times and are over the Colosseum. You have to bring that knowledge yourself.

They also can’t replace the judgment call you make when you’re standing in a piazza at 6pm and decide to follow the music instead of the itinerary. That’s still yours.

What they can do is handle the structural, time-consuming work of research and organization so that you arrive informed, prepared, and free to be present. For a solo traveler who plans their own trips without a travel agent or a partner to divide the labor, that’s not a small thing.

The bottom line

I’m not a tech evangelist. I write about technology because I’ve spent years watching it actually change how people live and work, and I’m interested in what’s real versus what’s hype. AI-assisted trip planning is real. It won’t replace the experience of travel — nothing will — but it has genuinely changed how I prepare for it. Faster, sharper, and with more confidence that I’ve thought through the things worth thinking through.

If you haven’t tried it yet, start small. Whether you are looking for a weekend getaway or a month-long solo journey, the best way to learn is to simply sit down and plan a trip with AI for a destination you’ve always dreamed of visiting. Pick a destination you’re already considering, open a conversation with Claude or Gemini, and just start talking through it. You might be surprised how quickly a trip takes shape.

Bryan Wolfe is a travel writer, solo travel advocate, and the founder of GoingSolo.Life. He writes for solo travelers over 50 who want to travel independently, with intention. He actually is a Certified Travel Advisor for Fora so if you don’t want to go the AI route, contact him today!