It can be done, but probably easier with two people. May make a difference whether you're doing it on the water
or on the trailer.
My Privateer ketch
has been re-rigged with 1/4" stays and half-inch turnbuckles, fittings, etc. so the masthead weight is great enough to rule
out simply "walking" the mast
up to vertical.
It's fairly easy to figure out how to use some mechanical assistance to get the mast
up -- I used a hand-cranked worm drive winch
mounted on the trailer. I have it modified to run off an electric
drill. My wife's on the ground, running the drill and I handle all the on-deck work. If you're on the water
, you could easily rig the mechanical assist at the bow of the boat rather than on the trailer. (In my experience, the mainsheet tackle is not enough.)
Single-handed, I think you'd want some temporary port and starboard stabilizer lines to keep the mast from yawing sideways as it comes up. There are lots of sites that can show you how to rig them.