What AI Taught Me About Planning the Perfect Vacation

Is AI ready to plan your travel? - Picture by: Nahrizul Kadri

Artificial intelligence is changing the travel industry, and I couldn't be happier about it.

At Rockport Tours, we use AI almost every day. It's an incredible research tool that helps us uncover attractions, compare hotels, estimate drive times, and organize information in seconds. Like many people, I wanted to see just how capable it had become.

So, while developing one of our upcoming tours, I decided to let AI take the first shot at building the itinerary.

This wasn't a simple weekend getaway. It was our new Country Roads tour, a week-long journey through the mountains and small towns of West Virginia and Virginia. If we offer the trip, hundreds of our guests may eventually experience it, so every decision matters.

I have to admit, I was impressed.

Within minutes, AI produced a route that looked polished and well thought out. It identified attractions I hadn't considered, recommended hotels and restaurants, estimated drive times, and arranged everything into a logical day-by-day schedule. If I had been planning a vacation for my own family, I probably would have started making reservations.

But I wasn't planning a vacation for my family.

I was designing an experience for our clients, and that's a very different responsibility.

Over the next week, I went through the itinerary one piece at a time. I compared hotel locations, recalculated drive times, searched for better values, and looked for ways to make each day flow a little more naturally. One adjustment led to another. Moving an overnight stop shortened the following day's drive. That created time for a more interesting attraction. A different route revealed a scenic stretch of highway we had overlooked. Changing hotels reduced our costs without reducing quality, allowing us to invest those savings where our guests would notice them most.

Even after a week of refining the itinerary, I wasn't finished. In fact, I'm still making improvements. That's the nature of good travel planning. There is almost always another opportunity to make the trip just a little better.

None of this means AI failed, quite the opposite.

It gave me an outstanding first draft. In a matter of minutes, it accomplished work that would once have taken days. It challenged some of my assumptions, introduced me to places I hadn't considered, and gave me a solid foundation to build upon.

What it couldn't do was apply experience.

It didn't know that our travelers would probably enjoy spending another hour exploring a charming downtown more than spending that hour on the bus. It couldn't recognize that a hotel with slightly lower online ratings might actually provide a better experience because guests could walk to dinner after a long day. It couldn't weigh dozens of small trade-offs that only become obvious after years of planning trips and listening to travelers describe what they loved and what they wished had been different.

I occasionally hear people wonder whether AI will replace travel advisors. After putting it through a real-world test, I don't think that's the right question.

A better question is this:

If AI makes you a better travel planner, what does it do for someone who plans travel for a living?

That's exactly what happened with our Country Roads itinerary. AI made me more productive. It exposed me to new ideas, gave me an excellent starting point, and freed me to spend more time doing what experience allows me to do: asking better questions, finding better solutions, and continuing to improve the trip long after the first draft was complete.

I believe that's where the future of travel planning is headed. It won't be people versus artificial intelligence. It will be experienced professionals using artificial intelligence to create vacations that are better than either could produce alone.

So by all means, use AI when you're planning your next vacation. Ask it questions. Compare destinations. Let it introduce you to places you've never heard of. It's one of the most useful travel tools to come along in decades.

Just remember that the same technology is available to everyone, including your travel advisor.

The difference has never been who has the tool; the difference is knowing how to use it.

AI doesn't replace experience, it amplifies it.