IS there anything available for talking back and forth with your riding buddy? Like microphone and speaker that will fit with helmet on? Any suggestions on what works well?

Chatterbox is probably the biggest known for this sort of thing. I have one, however, I don't think they are really up for the task of off roading. They were originally made for on highway motorcycles. None of the connectors have positive locks on them, it's all friction. I bought a GMRS X1 and my 2 buddies got the HJC (cheap ones). One of them ended up not working so I had 1 of my handheld radio's (Vertex UHF) reprogrammed to the HJC Channel 1 frequency (also a close match for the GMRS X1 channel 1). The GMRS X1 to my Vertex worked great. My other buddies HJC kept cutting out and we kept getting static. He had to keep fiddling w/ the connectors.

Another option is Collet, I've never used them so I can't comment, ATVers seem to like them.

Personally I really liked my handheld radio setup. I pulled the wiring out of my old race car and just installed it in the bike. All connectors either screw, clip or snap into place unlike the chatterbox. I never had a problem w/ a loose connection, also the power output on those radios is MUCH higher. Another benefit is as long as the manufacturers of other radio sets (Chatterbox, Collet, etc) tell you what frequency they are using (and it's UHF, which it usually is) you can get your radio programmed to that frequency and you are not 'locked in' to only talking to people that bought the same brand radio. Bad side is a single radio cost as much or more than an entire chatterbox setup. Then you have to buy the helmet kit, push button, etc.

The chatterbox would probably be your best bet if you have a SxS or 2up and ride w/ a group b/c then you can talk via the intercom w/ the passenger and via wireless w/ the rest of the group, but for pure wireless solution and about $600/radio to spend look at getting quality UHF radios from the likes of Motorola, they've been doing this for a while and know what it takes to get 2 way communications right.

Moto Com has a good set up.

The Moto-Com set up works great. My wife and I having been using it for years. Speaker pads and mic in the helmet, push to talk button at the handle bar grip.