A friend and I walked from Castle Rock to Big Basin. We certainly could have finished at Waddell Beach in one day. There is day parking available throughout the Skyline-to-the-Sea Trail and you can pick up the trail in various spots. This is a fairly easy, uneventful trail. We saw a deer and a turkey, felt (!) loads of mosquitos and heard the gunshots. All in, I’m disappointed to say that this is my least favorite trail in the Bay Area. It lacks gorgeous views throughout most of the trail and the logistics are cumbersome. Still if you want to log 30+ miles and end up in the beach, here are a few tips: call the Big Basin headquarters and check for trail closures the day before and aim for a cool day as the trail can get unbearably hot. And do NOT rely on a cellphone connection to call a Uber/Lyft, taxi or friend.