From the FAQ:
Q: How well do I have to ride in order to join?
A: You should be pretty comfortable riding your motorcycle or you really won’t enjoy the ride. You will encounter a variety of conditions; rain (or other weather), traffic, small bumpy rural roads, and typical staggered group riding formation in the guided rides. If you are signing up as a Self-Guided rider, you either need to be comfortable riding on your own or making new friends to ride with. If you are a newer rider and want to set a goal, we would suggest having ridden at least 3,000 recent miles before joining us and that you join us for the Fully-Guided done-for-you experience.