Don’t plan your trip with AI. Maverick it.

Everyone’s tried planning a holiday with AI (artificial intelligence). Type “10 days in India with kids”, get a tidy list, feel amazing. But let’s be honest: that’s a very polite Google search. The real fun starts after you’ve booked.

The bit nobody talks about

Your trip is locked in. Flights, hotels, transfers, tours. You’ve got a pile of invoices and itineraries from your agent, the airline and three booking sites, all in different formats. Accurate? Yes. Exciting? About as exciting as a tax return.

That’s nobody’s fault. Booking documents are built to confirm things, not to get people pumped.

Refine, don’t research

I’ve spent 28 years in adventure travel and tested every app that’s ever been thrown my way. This is the most fun I’ve had with any of them.

Here’s the trick. Don’t ask AI to do the legwork. Ask it to do the refining. Load in the documents you already have, then tell it about the people going:

• The kids want animals and anything that moves fast.
• Your partner loves gardens, so flag every one along the route.
• Grandpa wants to know where the good coffee is (and where the toilets are).

Then ask for a personalised itinerary for each person. Same trip, different lens. Everyone gets their holiday.

The India test

When I took my kids to India, I asked AI to add an animal emoji at every stop for the wildlife they might spot 🐘🐅🦚🐒, and a transport emoji for every leg of the journey: 🚆 ✈️ 🛺 🚙.

Simple. A bit silly. And it worked. They read it before every single leg, checking what was next and what they might see.

The big one: after the Taj Mahal, a long train from Agra, then a few more hours by road to Bandhavgarh National Park to find tigers 🐅. We spotted one on the very first day. Then not another stripe for the rest of our three days there. Didn’t matter. That one tiger had been on their itinerary since Sydney. That’s the difference between a schedule and an adventure.

Try it yourself

So we built it. Meet Tripp the Trekker, the newest member of Team Smarketing. Paste in the trip you’ve booked, tell Tripp who’s going and what they love, and everyone gets their own emoji itinerary.

The nerd bit

AI is brilliant at reshaping information you already trust. When you give it your real bookings, it isn’t guessing; it’s working from facts. That’s why this beats asking it to plan from scratch. Fewer made-up restaurants, more of your actual trip.

One safety tip before you upload anything: strip out passport numbers, card details and booking references first. The AI doesn’t need them to draw a tiger next to Bandhavgarh. Treat your data like your passport: only hand it over when you have to.

Why this matters for your business

Swap “trip” for “customer”. Most businesses send the same confirmation email to everyone. AI can take that one document and make it feel personal, without you rewriting a thing. Global vision, local thinking: one booking, made to feel like it was built just for them.

That’s what good AI does. It doesn’t replace the plan. It makes people excited to follow it.

Don’t plan it. Maverick it.

Brad, CMO (Chief Maverick Officer), Maverick Digital18 October 2026

Every idea here is mine, sorted with Claude's help.