In other words- you need to spend a lot of time planning routes, buying supplies, and working out numerous little details.
Or you can do what I did and sort of, um, wing it.
Don't get me wrong, I did plan quite a bit and prepare. I bought quite a few new supplies and updated old one (new dry-sacks, shoes, saw, cooking gear, water-filter, etc), and I knew generally what my route would be, but I was still doing some of this prep work on the day I was leaving. For instance- I didn't own a rain jacket and I was heading into the rainy season so I picked up a jacket a mere 2 hours before I want (and thank goodness I did!).
After I had most of what I needed my friends James, Lindsay and Chad picked me up. For some of them it was their first camping trip in 15 or 20 years. For others it was their first trip EVER. But they agreed to come up for a night or two to help me, as it were, acclimatize and to enjoy a little camping as well. One night in Barrie and then we'd be off the next day. It's going to be a fun trip.
This is a quick, poorly shot video of me moments before I left. I'm attempting to weigh my bag before I go.
After all was said and done the bag and my supplies clocked in at, gulp, 87 pounds.