Winter is a time of interesting and fun winds. We're pretty spoiled most of the year with wind pretty consistently out of the West/South-West. In the Winter an East wind is fairly common. When the wind is out of the East you cannot dock on the normal side of the dock with your main up, as it is now a downwind docking and you'll just run into it full speed (yes, skippers do this surprisingly often).
Launching and docking in an East wind
For your first Winter sailing, this will be a new and unique experience. Here are some tips for when the wind is blowing from the East:
For departure, after putting the boat in the water like normal, walk it all the way down the dock and push it around to the other side (by the pilings).
You'll have to use your foot a lot to keep it from banging/scraping as the wind wants to push it into the dock. Once it's around the other side you'll need to take the bow painter in your left hand and hug each piling so you can hand it off to your right hand so you can get the boat around them. Tie the boat off and from there everything is normal, including the push-off/backwards sailing away from the dock.
For returning, if you're coming towards the dock and you're on a starboard tack, you won't be able to depower if you try to dock on the normal side, but you should be able to slow sail up to the pilings side.
Check your slow sailing course and take a couple passes if you need to. It's a new docking experience so nothing wrong with circling around a couple times until you feel like you've got it. Bailing out of a docking when something doesn't feel right is a good show of seamanship, and if anyone on the bench makes fun of you for taking 3 tries to successfully dock feel free to throw them over the sea wall.
The other option for docking is to sail upwind, which would be past the Cal Adventures dock, towards the 3rd dock, drop the main, and sail jib alone back downwind. Furl or blow the jib early to give the boat time to slow down (it will take longer to slow than you think when going downwind, even with no sails out) and you should easily and gently reach the dock.
Another option, if you get between the docks and realize the wind is wrong, is to dock on the West side of the Cal Adventures dock, drop your sails, and bare poles or go jib-alone over to our dock. When single handing this may be easier than trying to drop the main while sailing.
As a general rule, regardless of the way the wind is blowing: If your main isn't luffing, abort the docking attempt and reevaluate the conditions. Do not dock!
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