Yes,you can raise the mast that way. It is easy for 2 people, not difficult at all. I have even done it by myself by running a line through the bow pulpit to the cabin top winch lifting and pulling at the same time. At least when I was younger! I have recently made up a contraption utilizing a broken Sunfish spar,block and tackle,1/4" braided line and a few eye bolts and snap shackles. All either free or from the hardware store. No expensive stainless here;not needed. With this I can now raise and lower the mast by myself again.