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Re: Help what sail to raise 1st?
When sailing away from a mooring generally raise the main first, except when a strong current has the boat pointed downwind and the mainsail would be plastered against the rig before you have it raised. Then sail away and out of the mooring field under the jib and go onto a close reach to raise the main.
When sailing up a mooring generally drop the jib first, except when a strong current will hold the boat pointed downwind at the mooring plastering the mainsail against the rig before you can get it down. Then sail up to the mooring under the jib and drop or furl the jib at the last minute.
If you sail to or from a dock the same principles apply. You certainly don't want to be sailing downwind into your slip with the main sail up.