Chile is rather serious cruising. If you have not done much igh latitude sailing before, please do some before you head down there. A nice trip round Iceland or up to Alaska are good ways to prepare.
The easiest way to Chile by far is from west to east, starting by going down the pacific.
Cape Horn is really no big deal by itself. You can daysail around it, with good anchorages right near by.
You need proper boat insurance or the Port Captain in Puerto Montt will not allow you to go down the channels.