They can be grouped by geographical growing region, wrapper, manufacturer, and to a lesser extent size. So say you have smoked a few maduros that you liked. Check to see where they came from and also try to see if you have a size preference. This may lead you to similar cigars, but you shouldn't be limiting yourself especially if you are just starting out. If your smoking experience is limited, go out and try everything you can. You'll probably start to see patterns emerging. I started out trying all sorts of cigars and I tend to lean towards 50 rg or smaller with natural wrappers. It seems like many people have a favorite manufacturer or two. If you find a cigar from a manufacturer you like, then try some of their other blends. Myself, I haven't found a Perdomo that I don't like, but YMMV. Good luck with your search and you've come to a great place for answers.