As GMFL said, prepare to motor. I sailed from Ventura Harbor to MDR in 11 hours with mostly good wind and current. The last 2 1/2 hours were under power, as the wind dies around 7 pm pretty consistently. With that said, going uphill, twice the distance will definitely require a stay over. I would suggest Marina Del Rey or King Harbor. Rounding point Dume is no easy feat and you want to hit that around 1:00 pm, so a nice morning sail through Santa Monica Harbor would be really nice.
1968 Cal 2-30