Every inquiry call starts the same way: a client tells me what they think they want, and my job is to figure out whether that’s actually going to get them the trip they’re picturing. Most of the time it lines up. Sometimes it doesn’t, and that’s when I push back. Not to be difficult, but because staying quiet in those moments does the client a disservice.
There are three requests I hear often enough that I’ve stopped softening my response to them: booking based on price alone, packing too much into one trip, and skipping travel insurance. Here’s why I push back on all three, every time.
“Let’s Just Book the Cheapest Flight or Hotel”
This one comes up on almost every call, and I get it. Nobody wants to overspend on a trip. But “cheapest” and “best value” are not the same thing, and the gap between them is where a lot of trips go sideways.
A cheaper flight often means a longer layover, a red-eye that leaves everyone exhausted on day one, or a connection tight enough that one delay turns into a missed trip day entirely. A cheaper hotel might save you $60 a night and cost you an extra 20 minutes of transit to everything you actually came to do, every single day of the trip.
I had a client push for the lowest-priced flight option to Rome once, a connection through a European hub with a 90-minute layover. On paper, it looked fine. In practice, a short delay on the first leg meant they missed the connection and lost most of their first day rebooking. The flight that was $140 more would have been a direct, and would have gotten them there on schedule.
What I push toward instead: I look at total cost, not sticker price. That includes time lost, stress added, and how a “deal” on paper actually plays out once you factor in the whole trip, not just the booking screen.
“We Want to See Everything in One Trip”
This one comes from a good place. People save for years for a big international trip, and the instinct is to maximize it. But an itinerary that tries to hit five cities in eight days usually delivers less than one that covers three cities well.
The math doesn’t work the way people expect. Every city change eats a half day, sometimes a full day, between checkout, transit, and check-in. Add that up across five stops and you’ve spent two of your eight days just moving, not experiencing anything. What’s left is a trip where you’re constantly packing, rushing to the next train, and seeing everything through the lens of “we need to get to the next place,” instead of actually being present anywhere.
What I push toward instead: Fewer stops, more time in each one. I’d rather a client leave a trip saying “I really got to know Florence” than “we saw twelve cities but I can’t remember which day was which.”
“We Don’t Need Travel Insurance”
I’ve written before about why this is a rule I don’t bend on, and it comes up on inquiry calls more than almost anything else. The reasoning is usually some version of “nothing’s going to happen” or “our credit card probably covers it.” Sometimes that’s true. Often it isn’t, and the gap only becomes obvious after something’s already gone wrong.
I’ve had clients need it for a canceled flight that meant covering an unplanned hotel night, a family emergency that required flying home mid-trip, and a lost bag with prescription medication inside. None of these are rare, dramatic scenarios. They’re the ordinary things that happen to a percentage of travelers every year, and the difference between having coverage and not having it is usually thousands of dollars.
What I push toward instead: Coverage sized to the actual trip, every time. Not the most expensive policy on the market, just something, matched to the real exposure of that specific itinerary.
Why I Don’t Just Book What’s Requested
I could take the easy road on all three of these and just book what the client asks for. It would be faster, and it would avoid an occasionally uncomfortable conversation. But that’s not what an advisor is for. If I only executed requests without ever pushing back, I wouldn’t be adding much value beyond a booking site.
The pushback isn’t about being right for the sake of it. It’s about having seen how these decisions actually play out on real trips, and caring enough about the outcome to say something before it’s too late to change course.
If you’re planning a trip and want someone who’ll tell you the truth about what’s actually going to work, not just book whatever you ask for, let’s talk it through. That conversation is where the best trips actually start.
