Help what sail to raise 1st?

[MITBeta]

Generally, main first, then jib. As for the questions about how to do this with no motor:

If on mooring, bow is kept into the wind by the painter.

If in open water, raising the main will keep the bow into the wind. You might actually end up sailing backward some, but that's okay (as long as you have the room!). Once the sail is up and you have some steerage way, you can raise or unfurl the headsail. With a roller furling headsail, you can deploy the sail on almost any heading, but with a hanked on jib, you'll also want to be into the wind.

Raising the headsail first and then the main while close-hauled is okay as long as you can actually sail like this with the headsail alone. Not all boat/sailplan combos will actually allow for that.

[DrB]

I nearly 100% of the time raise the main first and typically do it while on our mooring. The few times that I don't raise it on the mooring is if there is 15 to 20 kt winds as we need to go in a certain direction get into the main channel and sometimes the main and the motor be working against each other . Not that the we can't dump wind from the main, but it just makes steering more difficult especially as we leave the mooring. In these instances, we wait until more open water to raise the main.

The jib/genoa is raised second. Sometimes we do it running or reaching, but usually not when close hauled unless very light (6 kt or less) winds.

As far as which sail to drop first, usually it is the headsail, but I have dropped the main first and rolled in the head sail to a very small area and used it to sail onto a mooring more effectively in a breeze with two people. As we approach the mooring we come in on a close reach or "close haul" at about 3 kt boat speed at the right moment, spin the boat, furl the remaining head sail exposed while gliding into the mooring. We try to time it to "overshoot" the mooring by about the 3 ft which allows me time to pick up the pennants while the are slack and get them on before the boat gets blown backwards by the wind. My wife hates when we do this (no motor), but she knows it is a critical skill to have.

[sea_hunter]

Funny how things change over the years along with personal preferences. Sail trim primer for ketch
The "jib and jigger" sail combo is a proven ketch combination. After a century away from sailing fishing boats, especially with light plastic recreational sloops and cutters; traditional sailing methods are blown in the wind. I sailed for years pulling the main first but 50 years of experience has taught me there's more than one way to skin the cat. In a heavy blow, a jib and jigger set is the only way to go and is easily managed with an added reef for the mizzen and a close sheeted genoa. Single sticked boats are considered "easier" to sail and less expensive to maintain with half the hardware, but most schooner, ketch and yawl aficionados know better.

[Screaming Seagull]

Always raise main first and drop last. I feel more in control also find it easier to set the jib.

[rgscpat]

I'd think sailing's biggest problem is the sailors who hardly ever raise ANY sails.

[Ilverococoo]

I find much easier raising the main first and dropping it last.
I sail on a sloop and i have no experience with ketches so i can't really this is a golden rule

[Hudsonian]

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.

[asdf38]

I'm usually single handed or running the show myself. With main only I can tie off the tiler pointing down a bit and the boat will sail herself while I raise the genny. Much easier than the other way around.

I made the mistake once of sailing genny only with guests that couldn't be trusted with the tiller. Even though I wanted to raise the main once I got out I couldn't.