I’m the one who plans our family trips. Luckily, I actually love it — the researching, the booking, the piecing it all together is my kind of fun. But loving it doesn’t make it less work. A single trip is a startling amount of logistics and information to hold in your head: the flight time, the hotel address, the rental car confirmation, which night dinner is booked, which day is which activity. It all lives in fourteen different emails, a Notes list, three texts, and my memory — and I’m usually the only one who can find any of it.

This upcoming December we are planning a trip around Texas, and I’m trying something new: I’ve handed the whole tangle to my AI — specifically, AI Projects. Not a fancy app (I tried a few of these, never found anything that truly works for me), not a spreadsheet I’d abandon by day two — just one folder my AI remembers, and is easy to set up (and then keep up to date). Here’s exactly how I built it, and how you can build one for your next trip.

First, the 10-second version of “what’s a Project”

A Project is just a folder your AI keeps in its memory. You drop your trip stuff into it once, and from then on every chat you start inside that folder already knows the plan — no re-explaining, no re-pasting. Claude and ChatGPT both call it Projects; Gemini calls its version Gems. The free plans include it.

If you want the full tour — which app to pick, how the memory works, all the ways parents use it — that’s the previous post: AI Projects for Parents: Manage School, Trips & Home. This post is narrower and more hands-on: we’re going to build one, together, for a trip.

Step 1: Make a folder that only cares about this trip

Open ChatGPT or Claude, find Projects in the side menu, and hit “new Project.” Name it for the trip like you’d label a real folder — “Texas Trip,” “Spring Break,” “Grandma’s 80th.” That’s it. You now have an empty folder that’s about to become the most organized member of your family.

The reason you make a separate Project — instead of just asking in a regular chat — is memory. Everything you put here, and everything you ask here, stays here. Two weeks from now you won’t have to re-explain who’s going or where you’re staying. The folder remembers so you don’t have to.

Step 2: Get the itinerary in there — the easy way or the really easy way

There are two ways to load the trip, and both are fine. Pick based on how much energy you have tonight. Just make sure you put it in the “sources” section of the project — that’s what makes it stick.

The free, do-it-yourself way. Drag in whatever you’ve already got — the flight PDF, the hotel confirmation, a screenshot of the rental car booking, the list of ideas you started in Notes. It doesn’t have to be tidy. You’re not organizing a binder; you’re just getting everything into one place the AI can see.

The barely-lift-a-finger way. If your email is where all the confirmations actually live (be honest — it is), you can let the AI go dig them out for you. In a chat, ask it to comb your inbox and pull everything about the trip into a single document:

Check my emails from the past month and pull every confirmation and reservation related to the Texas trip into one itinerary document

It reads your inbox, finds the scattered confirmations, and writes them up as one clean summary. Then you save that document and drop it into the Project’s files — and now your whole itinerary is in the folder without you copying a single confirmation number by hand.

One honest note on that email trick: whether you can connect your inbox — and whether it’s free — depends on which app and plan you’re on, and which email you use. Reading and searching your inbox is free in a lot of setups now, but not all of them. If your app can’t connect to your email, no problem — the do-it-yourself way gets you to the exact same place. You’re just the one doing the copying instead of the AI. You can read more about connecting your AI app to your email in this post.

Step 3: Now stop planning and start asking

This is the part that actually earns its keep. Once the trip is in the folder, you don’t organize anything — you just ask, in plain English, the way you’d ask a very on-top-of-it friend. Some of it is the boring-but-precious stuff you’d otherwise be scrolling your inbox for:

What's the confirmation code for the rental car?

What's the address of our hotel in Austin?

Instant answers, no digging through six confirmation emails at the rental counter with a kid melting down next to you.

And then the questions that do the real planning work:

Create a budget tracker for the trip, add up everything I've already paid for, and estimate what's left (meals, gas, activities, ..).

Find a kid-friendly breakfast spots within walking distance of our hotel.

For our long drive day, suggest fun stops along the way that also have good food options for everyone.

Notice you never explain the background — the dates, the hotel, who’s coming. It already knows all of that, because it’s in the folder. And because every question lives inside the Project, you build up a running list of chats you can scroll back to — and find much more easily, because you only see the project-related chats. If, like me, you’d rather keep everything in one place than scattered across chats, you can ask your AI app to keep a single “activity tracker” document (more on the small catch with that below).

Keeping it current as the trip gets closer

Plans move. A flight time shifts, you book one more thing, someone changes the dinner reservation. You don’t have to re-do anything — just ask the folder to catch up:

Check my email for anything new about the Texas trip since last week, and tell me what changed.

Do that once a week in the run-up and the folder stays honest — just remember to save the updated itinerary back into the Project’s files (more on that below). If you find yourself doing this over and over (I like to plan my trips waaaaay in advance), you can actually automate most of this process via a scheduled task — but that’s a topic for another post :).

Step 4: Turn “things to do” into an actual plan

Here’s where a trip Project quietly becomes your travel agent. Instead of a dozen browser tabs of “things to do near Austin with kids,” you research right inside the folder — where it already knows your dates and where you’re staying — and have it build you a real list:

Suggest 10 things to do in San Antonio. For each, add all the logistics details, plus links to the website and Google Maps.

Because it knows the trip, the answers actually fit — seasonal attractions, nothing closed on the days you’re there, nothing that doesn’t work with a toddler. You get back something that looks like a plan instead of a pile of links: an activity tracker with hours, prices, and addresses, ready to use.

The one catch — and the easy workaround

Here’s the thing nobody (including the AI app) will tell you: what the AI figures out in a chat doesn’t automatically save to the folder. That great activities list you just built lives in that one conversation. The app may or may not carry this info to the next chat, depending on the current quirks of an AI-app feature called “memory”.

The fix takes ten seconds. Whenever you land on something you want to keep — the activities list, the day-by-day, the budget — just say:

Put that into a document I can save to the Project.

It writes it up as a file, you drop that file into the folder’s files, and now it’s part of the folder’s permanent memory instead of a chat you’ll lose track of. Think of the chats as your scratch paper and the saved documents as the actual trip binder. Do your thinking in chats; save the keepers as files. Want to add to the “activity tracker” later? No problem — ask it to build on the existing one, then download the new version and re-upload it to the Project’s files. (Most AI apps can’t edit a file that’s already in your Project directly — that needs a more involved Google Drive–type setup — so the quick manual re-upload is the reliable way to keep it current.)

Hand the folder to your co-pilot

And now to one of my favorite uses for this: you don’t have to be the only one who knows the plan anymore. On ChatGPT you can share a Project with other people — even on the free plan — so your partner and your older kids can open the folder and ask it anything you can.

That means the questions that usually route through you all day — “what’s our hotel again?”, “when’s the flight?”, “what are we doing Thursday?” — they can just ask the folder. You stop being the trip’s search engine, and everyone gets a straight answer without texting you mid-meeting. (Sharing works a little differently on Claude and Gemini, but on ChatGPT it’s free and takes two clicks.)

One caveat before you trust it with the flight

Treat the folder like a sharp, helpful assistant — not a source of gospel. It can misread a time on a busy confirmation, or answer confidently from an old file you forgot to update. So for the things that really can’t be wrong — the flight time, the check-out day, the reservation you’d cry to lose — glance at the original confirmation to be sure. The folder saves you the digging; you still sign off on what matters.