We're going to Rhodes this summer. Seven people, two separate bookings — us with the kids in one, my parents in another. The flight confirmations came in as PDFs. The hotel details were in a separate document. Meal preferences were scattered across a group chat. Passport expiry dates? Nobody had checked.

This is the part of trip planning that nobody enjoys. Not the dreaming-about-the-beach part. The part where you need to actually know what's going on, and the information is spread across five inboxes and a family WhatsApp thread.

So I handed it to my agent.

The setup

I created a task, uploaded the three booking PDFs — two flight confirmations and the hotel description — and told my agent what I wanted:

Sample prompt

Keep the Rhodes trip report updated with everything from the uploaded documents. Extract all flight details, hotel info, room assignments, baggage limits, and meal preferences. Research what we need to know about the destination — transport, local tips, things to do with kids, whether we need power adapters. Flag anything that needs action before we leave, and add important dates to the calendar. Run every morning at 09:00.

Then I walked away.

What came back

The first report had everything from the documents — flights, booking references, baggage allowances per person, meal choices, room assignments across both bookings. That part I expected.

What I didn't expect was everything else. My agent had researched the hotel on its own — pool count, kids' facilities, which restaurants were included, the Wi-Fi situation. It mapped out the local area: Rhodes Old Town, Lindos, Anthony Quinn Bay for snorkeling. It checked whether we'd need power adapters (we don't — Greece uses the same plugs as Sweden). It compared local SIM options at the airport versus eSIMs, with prices. It even pulled together a checklist of things to do before departure — verify passports, book the taxi to Arlanda, download the airline app for check-in.

I uploaded three PDFs. I got back a travel HQ.

It checks in every morning

The task runs at 09:00, every day. That's the part that makes it a travel assistant instead of a one-time summary.

Every morning, my agent checks if anything has changed. A new email receipt? Updated. Hotel confirmation for the room request? Added to the report. Digital check-in opening in 48 hours? Flagged. Passport validity deadline approaching? Reminded.

The report grows as the trip gets closer. Early on, it's mostly logistics. A week before departure, it's a complete briefing — what to pack, what's booked, what's still open, what to do when we land.

Ask it anything

Once the report exists, my agent has the full picture. I can ask it anything about the trip mid-conversation and it already knows:

"What's the baggage limit for the kids?" "Do my parents have the same meal preference?" "What's there to do near the hotel?" "When does online check-in open?"

I can also tell it things. "I booked the taxi for 5am on departure day." It updates the report, checks off the task, moves on. "My wife wants to change her flight meal to vegetarian." Updated.

It's like having a travel-obsessed friend who actually read all the documents and remembers everything.

The pattern

This works for any trip. A weekend cabin, a business conference, a two-week holiday with extended family. The ingredients are the same:

Upload your confirmations. Flights, hotels, car rentals — whatever you have as PDFs or emails.
Describe what you want tracked. Be specific about what matters to you. Some people care about restaurant reservations. Others want a packing checklist. Tell your agent.
Schedule daily updates. The morning check-in is what turns a static summary into a living assistant.

The next time someone in the group chat asks "wait, what time is our flight again?" — you'll already know.