David,

To you and all captains out there, no one appreciates all the responsibilities we must bear!

I'd pretty much agree with maytrix on the choices. I bought an alpha range wifi range extender several years ago and it really pulls in the signal but most of the sites are password protected these days. Going to shore might work out but I would think it would be a pain for all but casual use. I got the renport deal for $150 for 10 days at Sunsail so you might be able to negotiate. If it was $50/day I'd be thinking about a phone and a plan that allows tethering, a usb stick, assuming he has a usb port for communications or your own hotspot.