Can AI plan a company retreat?

More and more teams are turning to AI tools to help plan their company retreats. It sounds convenient—just plug in your trip details and let the algorithm do the rest. But when you're dealing with 50, 100, or 200 people, "good enough" just doesn’t cut it.

I tested one of these AI trip planners myself. Here's what happened—and why human planning still matters.

AI Travel Planner Mistakes: A Real Example

I asked a popular AI travel planner to organize a corporate retreat. I gave it the same brief we received from a client: an 80-person retreat somewhere in Southern Europe, with sunshine, access to the beach, plenty of outdoor activities, a balanced budget, and a thoughtful mix of downtime and experiences.

The first image it showed me? A stock photo of a bride and groom on their wedding day. Not exactly offsite energy. Then it recommended Marbella in June—a beautiful destination, but one I’d never suggest for work. It’s overcrowded, overpriced, and lacks the kind of local access you need for a smooth retreat.

A better choice on the Costa del sol? Mijas—still vibrant, but quieter, with easy access to the beach, Malaga's international airport, and a city full of museums, rooftops, and team activities. But unless you've been there, in person, during shoulder season, you wouldn't know that.

(Actual screenshots from the AI travel planning app) 

Why AI Retreat Planners Miss the Mark on Lodging

The AI pulled its lodging options from Booking.com—meaning no group rates, no behind-the-scenes insights, and zero awareness of what a corporate team actually needs.

One suggested apartment “sleeps five.” Technically, yes—if you’re okay with colleagues sharing beds and one bathroom. It also ignored our 4-star requirement entirely. The result? A plan that was off-budget, off-brand, and completely off base.

AI Activity Planning for Groups? Not Even Close

I specifically asked for sporty, group-friendly activities like sailing, windsurfing, and e-biking. What I got back: a wine tasting for six and a tapas tour for twelve. That’s not just tone-deaf—it’s logistically impossible for a group of 80+.

When I asked for revisions, the tool said "Sure!" and gave me the same results again. Because it’s scraping public marketplaces like GetYourGuide or Viator—great for tourists, not teams.

It even tried to price out an 80-person tapas tour for €90. The math wasn’t mathing.

What Human Retreat Planning Looks Like (Real Examples)

We recently planned a retreat for 80 people on the island of Brac, Croatia. Most restaurants there top out at 50 seats. But we made it work—twice. One dinner at sunset on the beach, another in a secluded olive grove under the stars. No booking engine would've found that. We did it through relationships built over time, with people who trust us.

When the ParkBee team wanted to keep partying after dinner, our local partner Maja called the only pub in town—which was already closed—and asked them to stay open. They hosted 30 guests until 2 a.m. That’s the kind of flexibility you only get when you know someone on the ground.

Sometimes it's about more than convenience. In Kotor, Montenegro, one of our guests—a woman from Argentina—fell down a stone staircase and severely injured her leg. She spoke only Spanish. Iva and I followed the ambulance, stayed with her and her son until 3 a.m., translated between them and the doctors, and convinced the hospital to let him stay overnight with her.

That's what company retreat planning really looks like. It's not just where you sleep or what you eat. It's about care, context, and making people feel safe, seen, and supported.

Human vs AI: What’s the Difference?

Ready for a Better Retreat?

AI tools are clever. But they don’t know your team. They’ve never rerouted a boat because of weather. They’ve never stood barefoot on a sun-warmed terrace and said, "This is the moment they’ll remember."

We have. That’s why it works.

Start planning your company retreat today.

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