15 Questions to Ask Yourself Before Planning Any Vacation

Ok, 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/editor 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. ( 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 ton 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 really good at dishing out some really 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 darn 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 exactly 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 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 and relaxing or am I hoping to take in the sights and experience a little culture? Or both?

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? Would it be better to go somewhere within driving distance?

7. What 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 movie theater near by?

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

9. Is food an issue? (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 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 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.)

On that note. I think I need another vacation. 


About: Mary Hawkins
Mary J. Hawkins is an accomplished editor, writer, and social media enthusiast who has been working in the digital media space since 2009. In a former life, she was the author and owner of The Mommyologist, a humor blog centered around the changes that happen after kids arrive on the scene. She is currently the full-time Senior Editor of Audience Development for CafeMom, and has been a part of their team for the past 5 years.  Mary also recently launched a lifestyle and travel blog called “Catching the Next Wave,” which centers around the new phase of life she’s navigating as a recently divorced single mom of one charismatic 10-year-old and a pint-sized Shih-Tzu.  When she manages to find time to detach herself from her laptop, Mary leads an active lifestyle. She has a strong passion for travel and welcomes every opportunity to explore new places and experience new adventures. She is also a huge fan of Pilates and Yoga – though she doesn’t get to class quite as often as she’d like.  Mary lives in a small town in the middle of Connecticut, though she’d rather live in the city, on the coast, or a combination of both.