20 Questions to Ask People About Their Vacation

Content Manager
Published 12/16/19
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One of the biggest perks of working for Miles is the generous open vacation policy. We love to travel, and it shows. From Africa to Asia to Antarctica, it seems like we’re always spotting a fellow coworker on Instagram, posting their vacation pictures from some far-off place. And I can’t complain—it’s great inspiration, especially as my travel wish list grows ever-longer and my comfort level of venturing to increasingly remote places expands. So when my colleague arrives in-office with that post-vacation glow, I want to know more than the typical two-step: “How was your trip? What was your favorite part?” (Because really, isn’t that what everyone asks?) I want to know details. I want to know the obstacles, the stuff they didn’t post on Instagram. What I’m really asking is: “Should I go, too?” Here are some of my favorite questions, but I’d love to hear your suggestions as well.

Happy travels!

1. What surprised you the most?
2. What was the biggest difference in how people live there, compared to here?
3. How was the language barrier/your ability to communicate with people?
4. What did you do for transportation?
5. What super-touristy thing did you do that was surprisingly awesome?
6. Was there anything you did or saw that you wish you skipped?
7. What was the best thing you ate on your trip?
8. What did you pack that came in handy?
9. What do you wish you packed with you?
10. Was it easy to find and buy things you needed along the way?
11. Did you notice any cultural norms that would be helpful for someone to know before visiting?
12. What do you wish you knew before you even booked your flight?
13. Did you experience any frustrations on your trip, whether related to the destination itself or the actual traveling?
14. If so, what should people be aware of in order hopefully avoid those frustrations?
15. What websites or services did you find the most helpful for planning/booking your trip?
16. What advice would you give someone going there for the first time?
17. What was the most enjoyable or relaxing part of your trip?
18. Did you go anywhere super beautiful where you felt like your photos just couldn’t do it justice?
19. Would you go back?
20. If so, what would you want to do next time you visit?