Last Friday I went down near Santa Cruz and celebrated the new year by running the Skyline to the Sea Trail from the beach to the crest and back. Wikipedia says it's 29.5 miles each way; my friends that measured it with their own measuring wheel say it's only a little over 26. It took me 15:58 to do it both ways. I made plans a week ahead of time to get a ride with a friend that was going to visit family in Santa Cruz, and the day we picked unfortunately ended up being the only rainy day all week, but it was still a pretty good run. I've heard some people be very enthusiastic about this trail, and not to be too disparaging, but I think those people just haven't hiked on the JMT. I mean, it's kind of a cool trail, there are some gigantic trees in the miles closest to the ocean, and I had a good time, but a lot of the trail is paralleling highways 236 and 9, and a good portion of it just has gigantic tree stumps as opposed to gigantic trees. If the Lost Coast and the East Bay Regional Parks made a baby, it might be the Skyline to the Sea Trail. Maybe I'm not giving it a fair chance because the views were socked in by the rain the whole time, but it didn't seem that it even had that many places where I would've had a view.
Sempervirens Fund. They're not waterproof, and you don't need them, because everything is very well signed, so I wouldn't buy them. Also, my friends hold a race on the trail in late April, so they've made a map of it.