Not sure what you mean by "safe". You can argue that it is not "safe" even on your own local streets. Depends on the attitude of the local cagers. The central coast is a popular cyclist destination, so locals are cognizant and aware of cyclists. For the most part, there are wide lanes out of traffic...but you will find spots where you have to cycle in the right lane for a bit. Safe? It's usually pretty safe, especially when cyclist ride together in any number. That old wildebeest syndrome ... safety in numbers. I'm big on "visibility". As a motorized two-wheeler cyclist, I'm into visibility and always being aware of my surroundings and what people are doing.

Can't offer any advice on the rides. I'm signed up for the Cool Breeze Century, but for the dbl-metric century. There is not that much climbing, but they have other rides without much climbing. Personally, I don't expect the wind to be an issue.