Anacapa would be the closest island to Santa Cruz and if you cross between
them early, you should be able to beat the afternoon winds.

I guess technically you are correct, but I read approximately four nautical
miles between Anacapa and Santa Cruz, and approximately five nautical miles
between Santa Curz and Santa Rosa - which at my typical cruising speed of four
NM per hour comes out to a fifteen minute differential. Big wow! The big bugger
here is the distance between campgrounds - which, as I stated earlier, is
substantial between Santa Rosa and Santa Cruz.
In the past there has been an issue with Island Packers (your ride over and
back) taking composite boats over to the islands. I don't know how that all
stands these days, but if any members of your group intend to use something
other then plastic boats you might want to make a specific inquiry as to the
current status on this issue.
Don't let the little details deter you from this trip. It's really not at
all as complicated as it sounds on this news group, and our channel islands
really are worth the effort.

Scott
So.Cal.