I've done it many times to CC, around the island, and out from the flats and back again.
Depending on recent storms, the water is usually pristine offshore, waves aren't bad, etc. There are no waves or beaches going from SP to CC. I think my first few RRregattas, there were 140+ boats going from SP to CC. Gots lots of trophies in a box somewhere from that Regatta.
NOw if they did it from SP to CC offshore, 1 day, kinda like dcay 1 of GT300, now that'd be cool. THAT would be a Rough Rider. But I can see why they don't want to do that for RR Regatta.
Go for it, lots of friendly people, etc.