combine anchor with rope and use it with the cannon at the end of the jetty
In the Brothel. With the very left hooker you need to do the bondage thing, after that you will have the rope. You might wanna talk with the woman behind the bar beforehand. Also when the hooker starts moving, let her go into the room first. Don't try to outrun her to be first in the room. That could prevent a bug from happening.