I highly recommend that you don't do this trip, especially in a 16 footer C-Dory. It would be very dangerous, even if you go North to South.
We have been doing the Bay/Delta Extravaganza for over 5 years, and we basically recommend that 16 footer's do not attend, and this is mostly inland waters, albeit can be very rough. The one year that a 16 footer did attend, the boat almost swamped itself on a very rough spot of the Sacramento River.
The 16 footer C-Dory is a great boat, but not big enough for San Pablo Bay and the San Francisco Bay, let alone the down the Coast.
I have been seriously thinking of taking my 22 footer C-Dory down the Coast for over 6 years now, and I still have not done enough preparation and had enough guts to do it yet.
The North Coast can be one of the roughest bodies of water in North America. This part of the Coast is not like the Southern California Coast in the Summer. I am experienced with both bodies of water and they are apples and oranges.
I have had my 22 footer C-Dory out the Gate and out of Bodega Bay many times, and at times it has been very hairy. On a good day it would be feasible for a 22 footer to make it down to Monterey or Santa Cruz out of the Gate. Beyond there, it will get dicey with regards to safe harbors, with the next safe point probably being Morrow Bay.
That all being said, I have heard of a wolf pack of 16 foot Boston Whalers gong from San Francisco to LA this summer. This is a bunch of crazy fishermen carrying a lot of jerry cans, and helping each other out down the way.
No offense, a 16 foot C-Dory is not a 16 foot Boston Whaler that is a very wet and uncomfortable boat, but is self bailing and probably unsinkable if kept running and upright. I know, because we have a 16 foot Boston Whaler also.
Again don't be offended. The 16 footer C-Dory is a great boat.
If you do the trip in your 16 foot C-Dory and live to tell us about it, please report it here. We all would be very interested!