Hey - that sounds like my dream too! Unfortunately I'm not quite at the point where I can actually see the year when I will retire...
Seriously though, you might want to take a look at the journals on
www.crazyguyonabike.com to get some ideas from the experience of others who are wandering on their bikes. Heidi Domeisen recently finished her almost year-long trek from North Carolina to Alaska and back again; you can find her journal at
http://heidi.crazyguyonabike.com. There are many other interesting journals there too.
Have fun planning and dreaming.
--- Denise