Wow, that sounds like a very fun trip to do
I have never sailed one of the Hobies, but it looks like one would do it with the right conditions. I'll say this though, I would start of with arranging the trip over and back utilizing a chase boat. If I could arrange one, great. If not, I would do another trip. It can get breezy in the channel which is ok, but it can get some serious swells and wind also. When the outrigger clubs have their annual race to Catalina each club has a chase boat, and they're not small.
After I had that taken care of both ways, I would look into the camping situation. Theres different campsites on the beaches around the island. I can't remember the name of the service, but one will drop people and their kayaks off at certain places, and you could probably find them on the net. Once I was sure I had a safe passage and a place(s) to stay while there, I would plan the rest of it.
Thoughts on the chase boat??
PerryC.
