This is not an exhaustive review—I just had a friend ask what I used for swimming headphones and I jotted down some thoughts that are barely worth sharing.
There are a couple of problems to solve with swimming headphones and I’ve tried a number of options.
The first is just the waterproof headphones themselves. I usually wear earplugs when I swim, so I want a headphone that has a nice seal so that it functions as a earplug as well. That also helps with the audio—it turns out it’s noisy to swim, so a tight seal helps with that. They also need to stay in—I’ve had trouble with earplugs with cords where they end up coming loose and/or falling out of my ears. I had a pair with bad over-the-ear clip things, but there are probably better ones of those out there.
The one kind I haven’t tried are the bone conducting headphones. Supposedly as long as they’re tight against your head they work fine. While I was writing this up, I see that there are $40–80 models, where I think they all used to be $200, so maybe I’ll try a pair sometime.
The other part is the audio player—bluetooth doesn’t work underwater, so unfortunately you can’t just have fancy waterproof bluetooth headphones and get your audio from your phone where all your music and podcasts are. You have to carry the audio player with you in the water.
I haven’t yet found a great solution in this regard. I’ll say that for me it’s compounded because I want to listen to audiobooks or podcasts while I swim, which means I need to manage the content more closely than if I just wanted to fill a player with some gym music.
There’s a company that used to modify iPod nanos into waterproof players, which was great because at least then you could Apple’s tools for how to automatically fill an iPod. That part was fine, but I ran into my issues with all the earbuds I’ve tried so far.
So my solution for now is the Sony Waterproof Walkman.
It’s a single piece player and headphones. The headphones have a nice seal and the design of the whole thing fits under my swim cap and it’s rare to have leaking problems. It could be a /little/ louder (I sometimes have trouble hearing a narrator when I’m swimming vigorously).
The audio management is lame - it mounts on my Mac as a drive and you just dump mp3s in a folder. So you have to get mp3s and any management is pulling files into or out of the folder. And the play controls are pretty much in-order or random. I gave up on podcasts and switched to audiobooks and even then I was having a lot of trouble with audiobooks with chapters restarting or skipping to the next one, so because I’m a nerd I bit the bullet and I just turn all my chaptered audiobooks into one big mp3 file and then every time I swim, one of my post-swim tasks is to open up the mp3 in an editor and just snip off the part I just listened to and resave it right on the little mounted drive. I finished a 10 hour audiobook this morning.