6 Weird Questions to Help You Discover Your Ideal Florida Vacation

One day, shortly after I graduated from college, my dad and I decided to take a fancy Florida vacation. And what I mean by fancy Florida vacation is whirlwind road trip in my trusty Honda Civic. I wanted to go on one last adventure before getting a real grown up job, and my dad wanted to visit family in the area.

The trip lasted less than 48 hours before we were fleeing the state, swearing we would never vacation together again.

Why? Because we had different goals for our Florida vacation. I wanted adventure and nature and crazy stuff like alligator encounters. He wanted relaxing days at grandma’s house, chit chat about the weather, and other boring, old people stuff.

Sure, I could have left him at grandma’s house and headed into the wilds of the Everglades on my own. But I was still young and dumb enough to think I had to do what my parents told me to do.

But it’s not just being young or naive that causes this friction. Everyone experiences it. How many times have you seen a grumpy old couple on vacation who can’t even agree on where to eat dinner? Or teenagers who look bored out of their minds while mom and dad happily snap pictures?

Part of the problem is that we think we know what the ideal vacation entails. Like we’re all the same and should want the same carefree tropical island expedition.

But that’s the same shitty logic that makes you keep buying skinny jeans when you know they won’t fit over your sugar thighs. And you don’t even like how skinny jeans look! Bring back bell bottoms, I say!

Some people like peanut butter and jelly, others like peanut butter and sardines. There’s no one right sandwich (although peanut butter and sardines sounds pretty gross), just like there’s no one right vacation.

The truth is, we are only on this earth for a short period of time, and we get an infinitely shorter period of time for vacations. So why the fuck would we spend our Florida vacation doing shit we don’t want to do?!

One of most common email questions I get is people asking where the best place to vacation in Florida is. This is impossible for me to answer without knowing more about them. For all I know, they’re really into competitive trampoline bouncing or filming empty plastic bags floating in the wind. How can I know what kind of Florida vacation they want when I don’t even know what kind of sandwiches they like?!

After doing a lot of thinking (and making a sandwich), I put together these questions to help you figure out what’s important to you and how to turn that into a vacation YOU will love.

These questions aren’t the end all, be all to discovering your life’s purpose or anything. In fact, they’re a bit ridiculous. But that’s because planning a vacation should be fun, not a chore.

If my dad and I had just asked ourselves these questions, we would have realized that we didn’t want the same type of sandwich vacation. But we also would have realized that we could still go on a Florida vacation together. We would just need to plan it so that we had some time apart to enjoy the things we wanted to do individually.

1. What makes you hold your pee until your bladder nearly bursts?

You know what I’m talking about. When you’ve been so engrossed in whatever you’re doing, that you subconsciously deny that you even need to pee until it’s almost too late. (And then ohmysweetbabyjesus, it feels so good to finally go.)

Or you’re so wrapped up in something that you forget to eat or drink for hours and hours, before finally realizing you’re severely dehydrated and about to pass out if you don’t hurry up and eat a damn sandwich. (What’s with all the sandwich references? I don’t know. They’re delicious. Just go with it.)

True story: I have done this while sorting screws. Yes, those little metal things people drill into wood to build stuff. I found a toolbox full of all different types of screws, and I spent several very enjoyable hours sorting all of them. Yes, I’m a freak.

What I later realized was that I’m not actually passionate about screws. I’m passionate about organizing things. (I’m not just a freak, I’m a control freak! Thank you very much.)

So when it comes to vacations, I really like the planning phase. I get to organize all the random information about a location into a well-planned itinerary. Hence, this website.

And although I still leave room for spontaneity, that general framework is important to me. So when someone decides to throw my whole Everglades gator adventure out the window in favor of sitting on the porch, sipping tea with grandma, I have a shitty time.

Maybe you don’t love planning your trip. Maybe instead you love getting lost in a fantasy world (hello, Disney) or helping people (voluntourism). Or maybe you just love food (who doesn’t) and want to eat your way across Florida.

Whatever it is, focus on the core principle of the activity that makes you nearly piss yourself, rather than the activity itself. Because that principle can translate into all kinds of fun vacation activities.

2. What fact about your life would make your 9-year-old self weep?

When I was a kid, I thought people who sat at a desk in an office all day were very important and also very stupid. Who would want to sit inside all day when you could be outside riding bikes or exploring the woods or discovering that male fiddler crabs wave their claws in unison to attract females (true story)?

I later ended up spending my days chained to a desk under the harsh glow of fluorescent lights. It made my 20-something-year-old self weep, and I’m sure it would have made my 9-year-old self weep.

It took many years for me to return to the wisdom of my younger days and realize that I just don’t like being cooped up inside. So vacations for me are all about being active in nature and the great outdoors. Not sitting on my butt, listening to people talk about their latest medical appointments and what triggers their psoriasis. Reminds me of all those pointless meetings I had to sit through, smiling and nodding along with the rest of the drones in order to make some higher-up feel important. No, thank you.

So think about the things you do now that would make your younger self shed a tear. Then don’t do those things while you’re on your Florida vacation.

3. If your house was being remodeled and you had to leave all day, every day, how would you spend your time?

We all get stuck in a routine – wake up, feed cat (obviously top priority), make coffee, brush teeth, check email, etc. We can go long stretches with nothing new ever happening. We wear the same clothes each week, eat the same foods, watch the same shows, blah blah blah. It’s like Groundhog Day.

We get stuck in mediocrity, and that’s a problem. It’s a problem because doing the same things over and over literally murders your brain. Okay, maybe it’s not that severe. But it is bad.

You know how sometimes (maybe a lot of times), you get in your car to go to work, and suddenly you’re sitting in the office parking lot with no memory of how you go there? That’s how your brain works when you’ve gotten too deep into a routine. It checks out and stops forming memories.

Seriously, think about the most memorable moments in your life. You probably don’t remember the 108th time you brushed your teeth. What you do remember are things that were different, new or unexpected.

But even worse than zoning out and having no memory of what you’ve done is the fact that excessive routine makes it harder to have fun when trying new things on vacation. Your brain follows the same neural pathways over and over, expecting the same results over and over. Then you try something new, and instead of getting excited or curious, your brain gets irritated by the unexpected. This is when you officially become a Grumpy Old Fogey™.

So what would you do if your routine were suddenly thrown out the window? You can do anything! No, you can’t check into a hotel and lie in bed scrolling through Facebook all day. Anything else!

Take a class, learn to surf, try new foods, take up cross-country cycling. Think about how you would spend your time, what kind of memories you want to create, and then do that stuff on your vacation.

4. How can you best make a fool of yourself?

If you’re like everyone else in the entire world, you have a thing you’ve always wanted to do, but you’ve never done it. It’s a thing you find your thoughts returning to over and over, a thing you literally fantasize about doing. But you never actually do it. Why?

Really think about your reasons for not doing The Thing. And if they have anything to do with what other people might think, then you are dooming yourself to a life of sadness and regret, my friend.

If you fantasize about ditching your dad to go play with gators, but you’re worried about what dear old dad (who knew you wanted to play with gators from the beginning and is actively preventing you from doing that) will think – fuck ’em. Go do it.

If you’re fantasizing about learning to surf on your Florida vacation, but you’re worried that people will think you look like an idiot – fuck ’em. Go do it.

If you’re fantasizing about just lying on the beach all day, reading trashy magazines, but you’re worried people will think you look fat in a swimsuit – FUCK ‘EM! GO DO IT!

Go against the herd mentality that says things like, “Respect your parents, even when they don’t respect you.” Or “People over 30 can’t learn to surf.” Or “Ladies must be thin and smiley at all times.” Just do The Thing that makes YOU happy!

5. If you knew you had 6 months to live, what would you do?

Okay, no one who’s planning a vacation wants to think about death. Really, no one wants to think about death. Period. End of sentence.

But thinking about the fact that one day you will no longer grace the face of this earth with your presence has a way of making you zero in on what’s important.

Your vacation is your chance to do what’s really, truly, deeply important to you. You’re letting go of routine and (hopefully) concerns about what others will think. You’ve thought about how you want to spend your days and what activities make you happiest.

So with all that floating around in your brain, what do you want to do before you die? Make it happen, cap’n.

6. How do you react when served a shit sandwich?

Shit happens, things go sideways, stuff sucks. No, I’m not being pessimistic. I’m liberating you from the mirage of a 100% perfect vacation.

Nothing is ever perfect. You will probably have to take a long, uncomfortable plane or car ride to go on vacation. You will likely try new things while on vacation, and some of them you might not like so much. Maybe that restaurant everyone raved about has shitty service on the night you visit. Or the maid who cleaned your hotel room before your arrival didn’t do such a great job.

How do you handle the unpleasantries of life? We all get served a shit sandwich sooner or later. So you might as well take it with a side of fries.

P.S. – If you want to find something everyone in the family will enjoy, check out these 42 things to see and do in the Florida Keys.