15 Questions to Ask Yourself Before Planning Any Vacation

Ok, you guys — I have a secret. And it’s one most of my family and friends already know, so I figured it was about time for me to just go ahead and admit it and put it out there for everyone to hear. Because I just can’t hide any longer.

Here it goes … (deep breaths) — Yes, I’m a writer by day, but I moonlight as an unofficial travel agent. Ok, so I don’t actually book flights and hotels for people or anything like that (though I have done that in the past). Somewhere along the line, I became somewhat of a “go-to” person for questions involving all things travel related, particularly when friends are planning summer vacations, weekend getaways, and everything in between. (Hell, I even get texts and phone calls about which restaurants to hit on any given Friday night of the year.)

Maybe it’s because I’m the daughter of a retired airline employee, so travel is in my blood. Maybe it’s because I’ve taken my fair share of vacations over the years and I paid attention and picked up and retained a buttload of info along the way. Or perhaps I’ve earned my unofficial travel agent status because I’m the resident trip planner in my own family. Whatever the case, I’m damn good at dishing out some really freakin’ awesome travel-related recommendations, so I figured maybe it was time to share some of my tips and tricks for making sure you don’t wind up crying like a baby upon checking into a hotel that looks absolutely nothing like it does in the damn online brochure in a destination that offers nothing but rest and relaxation when you’re looking for action and adventure.

I guess I’ll start with the basics — figuring out what the hell it is you’re after on whatever trip you happen to be planning.

Here are 15 questions you should ask yourself before deciding on the perfect destination. Once you have these answered, it makes narrowing things down a whole heckuva lot easier. (And yes, I guess I’ll need to do a follow-up post on where you need to go from there. Stay tuned.)

1. What exactly do I want? — (Seems simple enough, but I can’t tell you how many people I know who settle on a place to visit without knowing what they want to do on vacation, only to be disappointed after arriving. This is particularly important to figure out if you’re planning a trip with the kids.)

2. Is being right on the beach/close to the mountain/city important to me?

3. Do I want to be able to walk to said beach/mountain/city/town so I don’t have to drive everywhere?

4. Is this trip about sitting on my ass and relaxing or am I hoping to take in the sights and experience a little culture?

5. How much is in my budget? (A no-brainer, but this one often gets overlooked. For reals.)

6. Is flying going to be a huge pain in the ass? Would it be better to go somewhere within driving distance?

7. What the f*&% do I plan on doing with the kids on rainy days? Sitting in the room/rental and bonding, or is it essential to have a freakin’ movie theater near by?

8. How long do I wanna stay? (Many places have strict 3, 4, 7, etc. night minimums during certain seasons.)

9. Do I give a shit about the food? (Again, this one is kind of important if you’re traveling with the kiddos. My 6-year-old lives on a diet of chicken nuggets and grilled cheese, so it’s imperative that those two things are offered wherever we go. No exotic cuisine for him.)

10. Am I cool with cramming my family into a hotel room, or do we need to find a locale that offers plenty of home/condo/cottage rentals so we have more space to retreat to different rooms and ignore each other spread out?

11. When do I want to travel? Do I have time to renew my friggin’ passport before then? (If not, this helps eliminate quite a few options.)

12. How much stuff am I ok with packing? Is it going to be a hassle to have to pack nice outfits for dinners? Would it be better if we can just chill in bathing suits and cover-ups all week and not have to worry about getting all gussied up?

13. Will it bug the shit out of me if no one speaks English?

14. What types of fellow travelers do I want to be surrounded with? (Other families so your kids have kids to play with, adults-only, etc.)

15. How important is technology to me? (This is a big one that folks often forget to take into consideration. Believe it or not, there are still places on this earth that don’t have wi-fi or cable television. Sad, but true.)

Do you have anything specific you ask yourself before planning vacations?

 

 

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