Thanks for that tip. I have never heard of APRS, and it has quite the history! I am researching into that a bit more. It does require me to have a Radio Operator's license, so that may be a hindrance. Any other types of ways for the Arduino device to connect to the internet and send send GPS info while on the move?
I have found these wifi shields: http://asynclabs.com/
and then there is this for the iPhone: http://www.progical.com/
I am not really interested in jail breaking an iPhone for this or even getting into something vendor specific with phones though.