08/24/2026
I get asked some version of these same questions constantly. In DMs, on discovery calls, standing at a dinner party the second someone finds out what I do for a living. Here are eight of them, answered honestly instead of politely.
1️⃣ Is the "hidden gem" I've seen posted actually worth the trip?
🔦 If it's already on your feed, give or take about seven thousand other people have found it before you did. That doesn't make it bad. It just means the empty beach with no one for miles you're picturing probably isn't waiting for you anymore.
2️⃣ Is travel insurance worth the extra cost?
🔦 Listen, I know it seems like a waste of money. I question this on my own trips every single time. But I purchase it anyway because I've seen the things you never expected to happen... happen. Time and time again. Would you rather take the chance of losing $5k+ or $200-$300?
3️⃣ Do locals actually mind tourists?
🔦 Less than you'd assume, and more than you'd like, depending entirely on how you show up. Curiosity and three words in their language get you further than any itinerary I could hand you. How would you feel about someone coming to your home and not respecting any of your customs or traditions?
4️⃣ Are travel influencers exaggerating?
🔦 Umm... absolutely. Nobody is genuinely that thrilled about a four-hour layover. You're watching the best nine seconds of someone's entire trip on a loop, and the other twenty-three hours and fifty-one minutes looked a lot more like yours. Keep the FOMO at bay.
5️⃣ Is it actually cheaper to book on a Tuesday?
🔦 Not really. It's a comforting myth that makes you feel like you beat a system that doesn't even track days of the week. It tracks availability, market demand, and metrics. You should let price alerts do the actual work instead of this superstition.
6️⃣ What do I do if the person next to me on the plane isn’t respecting seat boundaries?
🔦 Babe, this one is completely on you and how confrontational you choose to be. Do I think it’s fair, no. But... is it always worth causing a big fuss over... also no.
I feel like the best option you have is to scout the plane and see if there are any other available seats, then ask the flight attendant if you can move.
7️⃣ Can I drink the water?
🔦 Some people say this is dependent on where you're traveling. If you're asking me... I say stick to bottled water whenever possible. It doesn’t matter if the water is considered to be potable. It’s probably still different from what you’re used to, and that just brings up the embarrassment of how to ask for diarrhea medicine in a foreign language.
8️⃣ Is tipping actually optional?
🔦 This depends entirely on where you are, and getting it wrong in either direction says more about you than you'd like for it to. The only way to know this is to either hire me or do extensive research before your trip.
If you're ready for someone who wants an advisor who’s going to give you the unfiltered answer… you’ve found your girl.
Have an embarrassing travel question you’ve always wondered about, but never asked? I want to hear them! Stick it in the comments or DM me. We’re going to get these answered without the formality.
