Currently I own a Honda Shadow (VT750 cruiser) and i love it. Poor man's Harley. Some day I would love to be able to own a good Harley!
Previously Yamaha Virago (very nice and easy little 250 cruiser)
Before that I did have a Suzuki DR250 Road/Trail for a while that I used to ride trails with, but run out of friends who wanted to ride trails, so now I just cruise country roads. By myself.
BTW:Looking for riding companion if anyone interested (nearby preferable but not essential).