Ever around a city as avant-garde (?) as Cincinnati, I've seen a few 'scooter riding clubs' ("mopedarmy"? "Scooter Mafia"?) - and they roll in big groups on a weekly or periodic basis. I'm sure that some of them are like some motorcycle groups (more posturing than riding...*some* motorcycle groups at least...) but if you are concerned about safety the group ride seems to be a better way to go. Look around your local internet/college/Hipster boards
These groups also sometimes advertise tech sessions- not sure how skilled you are with wrenching on small 2-strokes - I'd attend one of those just to see how skilled the group is (maybe you could teach them something...)
As a 750/650cc motorcyclist - I say grab that throttle and whack it ! 2 wheels is always the more fun way to go
-John