The Trips Worth Having a Person For
A lot of my clients start their trip the same way these days: a few searches, an AI planning tool pulled up in another tab, maybe a Pinterest board that's been quietly growing for months. And honestly, I think that's great. Those tools are wonderful for early inspiration, for narrowing down a region, for figuring out whether you even like the idea of an overwater bungalow before you go looking into what one costs.
Where it gets interesting is what happens next. A national survey released earlier this month asked travelers who already use AI tools a simple question: when it's time to actually make the call on a real vacation, who do you trust with it? Nearly half said they'd rather hand that decision to a person than to an AI. For Baby Boomers, it wasn't close: 59% wanted a human, only 15% wanted the AI. And 82% of AI users said having a real person to talk to still felt extremely or very important when they were booking.
So I've been thinking about why. Not in a defensive way, I promise, more out of genuine curiosity about what my own clients would say if you asked them the same question. And when I looked at what the survey found, it lined up almost exactly with the moments I hear about most.
When the trip has more than one traveler to think about
The number one reason people gave for wanting a person instead of an AI was coordinating group or family travel. If you've ever tried to plan a trip that needs to work for a toddler, a teenager, and a grandparent who isn't up for a 6am excursion, you already know why. It's not really about the booking. It's about someone holding the whole picture in their head at once: whose room needs to be near whose, who's celebrating a birthday on day three, who really just wants a lounge chair and a good book. That's the part I love most about family trips, honestly. Getting to know a family well enough to plan around who they actually are, not just how many rooms they need.
When the trip has a lot of moving pieces
Right behind family travel, people said they wanted a person for anything complex or multi-destination. This is honeymoon territory more than anywhere else. A week that moves between two islands, a proposal that includes a private dinner on one night and nothing planned at all on another, on purpose, because you asked for it that way. An AI tool can hand you a list of resorts. It can't sit with you on a call and ask what kind of mornings you actually want, or notice that you keep circling back to photos of the same kind of beach every time.
When something goes sideways
This one is close to my heart, because it's the moment I think about most when clients ask why they'd pay a bit more to book with me instead of a site. Over a third of people in this survey said a trip disruption, a canceled flight, a double-booked hotel, is exactly when they want a human in their corner. I've had that call. It's never fun in the moment, but it's also exactly what I'm here for. You've saved up that hard-earned time off, and the last thing I want is for you to spend an hour of it on hold with an airline. That's my hour to spend, not yours.
When the trip actually matters
And then there's the trip itself: a luxury booking, or simply one that means something. An anniversary. A honeymoon. The kind of week you'll still be talking about years later. People said they wanted a person for these specifically because the stakes felt higher, and I think that's exactly right. These aren't trips where you want to find out after the fact that the "ocean view" was actually a parking lot view from one particular angle.
What this actually looks like with me
None of this is a knock on planning tools. Use them for inspiration all you want, genuinely. But when it's time to turn the ideas into a real trip, this is where the concierge process earns its keep: a proposal built around what you actually told me, not a generic template; a video walkthrough so you understand exactly what you're looking at and why; and me, staying in your corner from the moment you book through the moment you're home, handling the excursions, the reservations, and yes, the occasional canceled flight, so none of that has to be your job while you're supposed to be on vacation.
If you're somewhere in the middle of planning a family trip, a honeymoon, or a getaway that actually matters to you, I'd love to hear what you're picturing. That's always where I like to start.
