Redwood City and the South San Francisco Bay is a wonderful place to sail and an excellent place to learn. The conditions are usually ideal for sailing. San Francisco is about 20 miles away, although Coyote Point can be reached in enough time to spend a few hours and return in a single day's sail.
The wind comes up to 20 - 25 knots in the afternoon just about every day in spring, summer and early fall. It's generally a lot warmer during the sailing season than in the North Bay. Sailors can usually go out wearing shorts and tee shirts. In the winter the weather is more of a mixed bag with a few good sailing days mixed between periods of calms and winter storms. Sailing up the Bay is usually a beat while the return trip is an easy run down the bay and then a reach in the channel.
Sailing is good in the Redwood City Channel and outside the channel in the South Bay. The wind generally blows across the channel making it easy to sail both directions in brisk wind and flat water. The afternoon chop in the South Bay is not as severe as in the North Bay but is higher when the current is ebbing against the typical northwest wind.
For more information check out the South Bay Handbook, by Bob Diamond