Sounds like you are going to have a great trip; good time to do it. Expect light winds during mid-summer but be ready for the occasional clear air gale. It's important to keep a careful check of the weather reports and weather-fax forecast so you know what is ahead of you. There is a weather fax device that hooks up to a laptop so you can download the data; I have the model and I will lookup/post here. You can buy it at Ham Radio Outlet in Oakland for ~100 bucks or so.
There are lots of places to stop along the way; I'm sure more than I can think of to post here. Here are a few thoughts:
Half Moon Bay - Great first day trip place to stop in; be mindful of the entrance channel between the north and south reef
Santa Cruz - you can either anchor out and dinghy over to the wharf or go in to the marina south of the lighthouse. Don't go in to the marina if there is swell from the south; breakers can form in the channel. This usually only happens in the winter.
Capitola - I believe they have a public mooring field
Monterey - Another great place to stop and check out sights, food, aquarium. They have had problems with sea lions boarding moored boats; so I would request a slip if you see any sea lions in the marina.
Morro Bay - Nice place to stop in before heading south of Pt. Conception. Great place to go kayaking; rentals available if you are not taking your own.
Make sure you have a good weather window for rounding Pt. Conception; particularly when sailing north. Many people round it either in the night when the wind is down (motor-sail) or wait for a calm day. It is sort of like "the slot" on SF Bay; except with bigger winds and seas.