There's lots of info on this board on going aloft. You also might want to try a search here for Mastmate -- a nylon webbing mast
ladder that allows you to go aloft without someone winching you up or tailing the
line. I bought one earlier this year and it made going aloft quite easy. There are a lot of TopClimber fans here as well, plus people who will recommend assembling your own solution using climbing gear. For me, the Mastmate was the most straightforward -- just like climbing a
ladder (albeit on a boat). Mastmate's web site is at
MastMate.com.