Mya

If you've got a motor, I would use it to idle into the wind, and either tie your rudder down or move it down into the feet well to keep it from moving too much.

Remember though, it's only a matter of time (depending on wind conditions) before the boat will start to move away from the wind. So you've got to be fast.

In order to do that, while back at the dock before leaving, I would have all of the slides in the track and ready to go, with the rope cleated off ready to be pulled. Then I would just use one piece of rope to reef knot the main down to the boom, to keep the sail from flapping around. Leave a loop in the knot though, because this allows you to remove the knot in one motion in just a split second.

You pull the string and poof, it's off.

So then you just idle into the wind, run up to the mast, pull your rope loose, uncleat the halyard, and start pulling.

Once the main is raised and winched, you scamper back down to your cockpit to correct whatever-the-hell-direction your boat is now trying to go. Run a halyard back to you if you can.

You might need to pick up another block to act as a turning point. That way you can hoist most, if not all of the way from the cockpit then, if you need to, you can quickly go forward when you're head to wind and secure it.

Another way, which would be a bigger pain in the ass would be to anchor, hoist, then raise anchor and sail off.

The third way takes some skill and a small boat like the Catalina 22.

It would be using your body weight to keep your boat head to wind while hoisting. As a dinghy sailor first, this makes sense to me but learning to control your boat with your body weight can be challenging, especially if the boat is moving backwards.

Then if your jib is a roller furling, you just get it going from the cockpit, and now you are ready to go.

So to recap: Motor out and pick up a mooring, or anchor somewhere shallow on the windward side of the river/harbor. Then you can hoist the sails with no rush, and slip the mooring or pull up a couple of yards of chain and sail away.