welcome to riding with music! I've three options for rolling with tunes. Zumo, generic mp3 player, and cell phone. No speakers, especially handlebar mounted ones, as ear buds work most excellently.
Etymotic 6i Isolator Earphones.
I wear either ear plugs or the etymotic buds whenever operating a motorsickle. The etymotics take longer to wear as the wires need to be attended to. routed under the jacket. Have the 5mm audio cable unnested from behind the ignition cover, etc. I hardly ever listen to music when riding locally. Heck by the time I suit up the last thing I want to do is fiddle with wires.
So when is a good time for the hassle? Tank to tank riding. Hands down. Seems like I'll be listening to music on my way up to Silver Spring MD May 10th and then up to Dahlonega May 16th. The zumo has a decent mp3 player. I control the volume and can select the tunes from the zumo which is mounted on my left handlebar. And the zumo also tracks detailed routes compiled from painstaking encounters with google maps. Zumo. Music and maps. Dang, reminds me of the third season finale and the fourth season premiere stardates 43989.1 - 44001.4. The Best of Both Worlds. lol