Surfing Photography? Do I use a flash?

Depending where you are and the time of day you might consider a large Plexiglas mirror held by an assistant. With some practice you can light a subject from a long way away.

(hint: because it's Plexiglas you can bend it to focus or diffuse the beam from it to suit your subject)
 
I shoot surf/kiting/windsurfing photography out in the water with a housing kit and flash will complicate things from the get go.

Honestly...I wouldn't touch that housing you are going to use. Going out into the surf means going out into very violent water and you want to make sure you have a solid housing kit to protect your camera. I have seen first hand a few camera's get trashed in the same housing you are looking at from a wave dunking the photographer and then thrashing the camera. I would hate to see your 17-55 and 30d get wet. Zooming in that housing is going to be really hard too.

I have been using Essex Surf Housings and they are awesome : Link. I am #3 on the list for the new one for my 7d and can't wait to get it.

Flash: I don't shoot flash with surfers in waves. I will shoot flash at dusk when I'm shooting kiteboarding and windsurfing in the flats or chop. Usually it's a set of vivitar 285hv's on some heavy duty flash stands. They are triggered by my Alien Bee's Cyber Sync's. I built some waterproof housings for the flashes and the trigger. Sync speeds on a 30d are 1/250.
 
the first two pictures you posted the photog was not in the water. I use my 10mm all the time for surfing. I have the ubxp 100 and having that fill flash when i need it really helps a lot.

You cant use a big aperture when you are shooting in the water. It will be impossible to focus the surfer at f/ 2.8. And for the statement that said use iso 200, disregard that completely. If anything you should use a higher iso.
 
all this was good advice. my only advice is be EXTREMELY FREAKIN CAREFUL when it comes to ur camera gear and salt water. i cant stress it enough!!! i just lost my rebel xs body and possibly my $1400 100-400L because of salt water.
 

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