With a deck
, it is do-able with much forethought and a few helpers. With a keel
, things get tricky. You have to actually lift
the mast. Two other boats, one on either side, can lend a hand with winch
. Never done it myself, with a keel
stepped mast. With a deck
stepped mast, you can use the boom for leverage to get it started up. Best way is to move the gooseneck down to the base of the mast so you aren't pushing a bow into the mast. You got to get it up to a reasonable angle before stays alone will have enough leverage to raise it. The boom gives you the upward pull on the mast that you need. You MUST maintain firm lateral control with the shrouds or you invite disaster. I have (ahem) "seen" just such a disaster and it aint pretty. Especially when your helpers are halfway through the second case of beer
and are ready to blow the scene and hit the bar.
When possible, use a crane. Takes jsut minutes and USUALLY does not result in a calamitous catastrophe.