Questions to Ask Before You Choose a Travel Advisor
10 Seconds: Not every advisor is the same, and not every advisor is right for your trip. Here are the questions worth asking before you hand somebody your vacation, and the honest answers you should expect back.
You’ll Learn:
- The questions that actually tell you something, versus the ones that just sound smart
- Why “does this cost me extra” has a more surprising answer than you’d think
- How to spot an advisor who’s actually working for you versus one who’s just processing your card
- The one question almost nobody asks that you absolutely should
“Does This Cost Me Extra?”
Let’s start here, because it’s the question everybody’s afraid to ask and the one with the best answer. For most bookings, no. Hotels, resorts, and cruise lines build a commission into the price whether you book direct, through a website, or through an advisor. You are paying that commission somewhere no matter what. The only difference is whether it’s paying for a website’s server costs or paying for a person who’s watching your trip.
Where a fee does show up is on the genuinely complicated stuff. Fully independent, custom built trips, personalized road trips with a dozen moving pieces, lengthy multi destination itineraries that take real research and real time to build right. That’s not a fee for typing, that’s a fee for the hours it actually takes to put something like that together. A good advisor will tell you this plainly before you ever get started, not bury it in fine print after the fact.
“How Many Times Have You Actually Been Where I’m Going?”
This one separates the advisors who sell a place from the advisors who know a place. Anybody can read a resort’s website. Not everybody has stayed there, eaten at the restaurant that’s actually good versus the one that photographs well, or knows that the “ocean view” category means something different than it sounds. If the answer is “I haven’t been, but I’ve heard great things,” that’s not disqualifying, but it is worth knowing.
“What Happens If Something Goes Wrong While I’m There?”
☎️ Jani’s Tip: Here’s the honest answer, and it’s not always “call me first.” Sometimes the fastest fix is standing right in front of the person who can actually fix it. A nicely worded conversation with the concierge, a call to the in-destination specialist your resort or cruise line provides, or heading straight to the airline counter often gets you a solution faster than routing it through me first. What I do want is for you to loop me in at the same time, a quick text works fine, so I’m working the problem from the back end while you’re working it in person. I’ve had clients call me from a broken down rental car in the mountains, and clients who handled a room mix up at the front desk themselves in five minutes flat because they were standing right there. Both are the right move. A good advisor should be honest with you about when it’s faster to speak up in person than to wait on a phone call.
“Are You Working With My Budget or Around It?”
A good advisor asks what you actually want to spend and builds toward it. A less good one shows you the prettiest options first and lets you feel awkward about saying no. Watch for whether they’re asking real questions about what matters to you, private pool, walk to the beach, kid friendly pool versus adults only quiet, or just showing you a catalog.
The Question Almost Nobody Asks
Ask what they’d tell you not to book. Any advisor with real experience has stopped a client from making a mistake, wrong resort for their group, wrong time of year, a room category that wasn’t worth the upcharge. If they can’t think of an example, they either haven’t been doing this long, or they’ve never told a client no.
Quick Reference
One Last Thing…
If you ask these five questions and the answers feel honest, you’ve probably found somebody worth working with, whether that’s me or somebody else. I’m always happy to answer all five myself, no pressure attached.
XOXO, Jani ~ Personal Travel Advisor | Take Time To Travel, LLC
Updated September 2026
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