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The weather is a little more iffy in the winter and there isn't as much wind, but sailing is absolutely a year-round activity here. Racing too, never stops. Just take a look towards the water on any nice winter weekend day.
 

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Some of the best sailing is in the winter. Many times you will find yourself nearly alone on the bay. I always loved going out in the rain, and sailing. Sometimes the wind is benign, and sometimes it can be blowing stink with half the bay foam from capping.......i2f
 

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STARBOARD!!
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OK; first this is NOT the end of the sailing season here! Winds don't become light/variable until November; with heavy winds during storm cells. So the "season" is really only about 1/2 over (just like baseball).

Your question about winter sailing is a good one; what happens is the number of "good" days is fewer but there is definitely some great sailing during the winter here. Winds are more variable/light but it is a GREAT time to get to know a new boat without the heavy 25-35kt winds you find in "the slot" (between Angel Island and SF) during the summer months. Just watch for storm systems and be prepared to bag your plans for the day if there is a clear air gale that NOAA incorrectly predicted for. We have had that happen more than once; but if you are more careful about not setting full sails out before you get out onto the bay you will be fine. I sail out of Richmond and during the winter we only set the main before exiting the protection of the jetty and hills along Pt Richmond; because sometimes it's blowing 40kts from the due north and we would not want full headsail and main in the event that it was.

On days when the wind is light you can get some great light air practice and run large headsails that normally would be too much sail for the regular summer winds here.

When I bought my boat we did not splash until late August; which turned out to be perfect for the reasons I have mentioned.
 

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STARBOARD!!
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Yep; I mostly wear a fleece with waterproof/breathable liner (Ronstan) and my foulie pants as a wind breaker on the legs. If it's really cold I will wear the foulie jacket over my fleece. Get a pair of the full finger Gill gloves that have the neoprene upper and your hands will stay warm on those clear/cold days.

The summer can be cold here also if the fog is in; as Mark Twain said "The coldest winter I ever spent was a summer in San Francisco" (and if it's true he did not say this as Snopes.com claims he should have)
 

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Cal 9.2 SilverSwan
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I raced MORA in 1978, out of St Francis Y.C. ocean venue. Other races we did included the Vallejo race, one of my favorites. We did the summer series and a few races in the winter on the Berkely circle. It can be quite cold and dress for it. Going from memory, it seamed like the rainly season was from Nov through March, but still had plenty of sunny days to be out on the bay, just less traffic.
 

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Agree with I2F and KeelHaulin, there is some great sailing in the winter as long as you watch for the fronts (and are particularly careful if going out under the bridge). There is something really amazing about being out on the Bay during the winter and having it to yourself...:D
 
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