You are so going to regret asking this question.
I have spent more time worrying about my park bag and its contents than any other single aspect of my WDW trips.
Buckle up.
Before we even start we have to talk about rain.
My greatest fear when it comes to WDW is rain. So even before my first trip I was trying to figure out rain contingencies. I had found some amazingly comfortable shoes for the long days of walking, but they were not waterproof. So I figured I’d carry a second waterproof pair. After trying all manner of possibilities — flip flops, sliders — I settled on Crocs. OK, they’re ugly, but they’re very light and they’re waterproof.
I figured a small backpack would be the way forward. After much shopping around I found this:
It was very expensive (over $100) but beautifully designed and made, with all kinds of zippered pockets and whatnot. It was small, but big enough for the Crocs.
Perfect!
I arrived at the house I was staying in at around 4pm on my first day, having flown in from the UK. It was immediately obvious that a backpack was completely impractical in the Florida heat and humidity. It would have been miserable to carry around. So I abandoned it — and, indeed, never used it. I recently sold it on eBay at a considerable loss.
A few hours later I set off for MK carrying very little as it was early evening and beautifully clear. All went well. I had a great spot in the Plaza Gardens for HEA. Then something happened. The HEA narration really moved me. Something about being who you are. As the park closed I walked down Main Street and into one of the expensive shops on the right. I found this bag:
OK, so it’s a woman’s bag, but HEA had taught me not to care about things like that. It was perfect. Easy to carry, exactly the right size and — damnit! — I liked it.
But I didn’t see myself walking around my hometown carrying it. So I gave it to my friend (in the picture) when I left.
A year later I was back. This Crocs plan hadn’t worked out — they slide all over the place if it’s raining — and I abandoned the second pair of shoes plan. I’d just take my chances with rain and rush indoors before my shoes got soggy.
But what bag to carry? I had a (masculine) over-the-shoulder bag, similar in style to the one @missoverexcited is modelling in her photo. I put my poncho, glasses case, phone, medication, wallet and so on inside. But the over-the-shoulder thing just didn’t work for me.
So I trawled the Disney stores looking for something better — alas I could find nothing. I had more luck at UOR, where I found this:
(Magic Band included for scale.)
In many ways it was perfect, but I never really liked it. In particular I didn’t like the fact it had a UOR logo on it. But it worked well for the rest of the trip.
My next trip was in December. I discovered that Florida isn’t actually that hot at that time of year and I had a couple of coats — a padded gilet for when it was “cold” and a very light raincoat for when it was raining. Both had various pockets, including enormous ones at the front. I didn’t need a bag at all thanks to these — a wonderful-time saver at bag-check.
The gilet:
The raincoat:
Which brings me to my next trip. Whenever that will be. Ahem.
I searched high and low trying to find a tote like the Minnie Mouse one I used in my first trip. Except a “masculine one”. It turns out there is no such thing. No-one makes them.
Oh, yeah, I nearly forgot: why back to a bigger bag? Because I had the genius idea of buying water shoes for when it rains, so it needed to be big enough to carry these around.
Anyhoo, eventually I found a bag on the Herschel website. I searched for “man’s tote bag” and it came up but, well, you decide.
Yeah. Huge mistake. It’s supergay.* Look inside:
Obviously that was a huge mistake. But returning it was going to be a hassle and I couldn’t be bothered. Another $80 down the drain. (I actually tried to sell it on Facebook Marketplace: no takers. So then I tried eBay: it got one bid of $5. I got a friend to shill for me. Which pushed the price up to $6. Which was the winning bid. So I still have the damn thing.)
My next candidate bag appeared when I saw one of my students had a very small sports bag. I loved it and thought it was perfect.
It’s big enough for a pair of shoes and a few clothes. It’s small. Perfect!
Until I started thinking. Do I really want to be carrying this thing around all day? What am I even going to carry with me?
To which the answer is:
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My super light raincoat. It rolls up into a pretty small ball and is way better than a poncho.
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My glasses case. I wear sunglasses outside, but need my regular glasses inside.
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A few medications that I take daily.
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My phone, with a battery case so that it lasts all day even in WDW. (I prefer not to carry it in my trouser pocket. I like my clothes to feel light at WDW. It’s hot. And humid.)
And a few other items, but more of those later.
Then I saw this:
(Tennis ball included for scale.)
It’s something I already own and have done for years. It’s small, light, rigid, comfortable to carry. Perfect, surely?
My only concern is that it’s hard-sided. You can’t squish it into tight spaces. Of course the flip side is that this means it protects the contents very well.
It’s my current preferred option.
And it’s got me thinking about what else I might want to carry around. In particular, I’ve become obsessed with miniature things.
It’s big enough for an iPad mini. So I bought one. (Well, I traded in my iPad Pro for one.) Why would you carry one around with you in the parks? Why not? It fits. It’ll be secure.
But in the last week or so I’ve had my Best Idea Ever.
During my first trip I did quite a few of the sit-down shows at WDW and I found the bleacher-style seating agonisingly painful. Although I’m grotesquely fat and no-one will ever love me, I have quite a bony ass.
So I’ve avoided those shows but next time I want to try some again. So I started googling “stadium cushion”. And eventually I found this:
It’s beautifully made. It inflates in about one and a half blows. It deflates instantly. It’s exact the right size for my bony ass and it folds down to a size that would fit in your outstretched hand:
It’s the nicest thing I’ve ever bought. I love it.
My most recent purchase was these:
Stainless steel straws. I hate the paper ones — they go soggy too quickly. I’ll carry a couple of these bad boys around in my case along with a cleaning brush.
I think it’s possible — it’s not impossible — that I will have the best day bag and contents of anyone in WDW. Ever.
Oh! I forgot about the water shoes. What of them? I’ve decided they’re a dumb idea. I’ll just hide from the rain when it rains like I have done during every other trip. It would be too much hassle carrying them around and changing into them and back out again. Well, maybe I’ll take them if rain is forecast, or if I’m planning to try KRR. Or the resort pool.
*Oh calm down. I’m gay. I’m allowed to call things supergay. It’s one of the perks of being gay. And there aren’t many, believe me.