In my misspent youth I would smoke just about any cigar; machine made, hand made, hand rolled, good, bad and ugly all graced my lips from one time to another. In my old age I have come to develop distinct preferences and will use this post to list mine. I invite others to follow suit.
I like dark cigars. Those cigars using the maduro or ripened and fermented leaf of the tobacco plant as a wrapper seem to satisfy my tastes for complex intense flavors.
I like long cigars. I often and incorrectly smoke a cigar down to the point my that my lips are burning. Those who have smoked cigars long enough will know that somewhere around 70% into the cigar the flavors will become harsh and bitter. All things being equal (quality of tobacco, construction, humidity) a longer cigar will give more time to enjoy and explore the flavors
I like thick cigars. Again, it has been my experience that thicker cigars are more forgiving of variables (construction, fast smoker, humidification issues) while at the same time almost always provide a much more complex smoke.
I like hand made cigars. I am convinced I can taste the difference between a machine made and a hand made cigar. The cigar roller is an artist. To see one at work is a thing of joy and beauty. To enjoy their art is to partake in their soul. Machines have no soul. Cigar's made on machines are soulless.
I like aged cigars: Some cigars, especially those with lighter wrappers can suffice with 6 moths to a year of aging. But those that are thicker ring cigars and especially those with the maduro wrapper benefit greatly from extended aging in a proper humidor exposed to Spanish ceder at a humidity level between 65%-70%. Smoking one of these before a year aging in your humidor is not allowing the full greatness of the cigar to emerge. This is why many, like myself, keep a few hundred cigars in humidors. This allows a rotation of new cigars coming in and aged cigars coming out. Most also keep a small portion for really long term aging. I have some cigars that are 15 years old. Most, though, age 3-5 years before getting consumed.
I like properly stored cigars. Nothing and I mean nothing is more disappointing to a cigar smoker than to light up a stick to find it is either under or over humidified. Over humidification will crack wrappers, distort the smoke by not allowing the cigar to burn correctly or at all. In extreme cases you can see mold growing on over humidified cigars. Under humidified cigars are just a damned shame. The essential oils in the tobacco just float off when the humidity level is allowed to plummet. Although under-humidified cigars can be, in many cases, re-humidified, they always loose a certain amount of flavor and character. Under-humidified cigars burn like a forest fire; releasing tars and horrid tastes.
I like to enjoy cigars with close friends. Although I am an intensely private person I do admit that fine cigars are best enjoyed in the company of others. Although, I do enjoy a cigar in the dark winter evening; by myself, contemplating my private thoughts. Those moments that I recall the clearest and with fond feelings are those shared with close friends and good cigars. Usually there was talk of children, holidays, guns and the future after a superb meal. These are the moments that make life worth living.
I like to enjoy cigars with good spirits. I think that almost any liquid will improve the smoking experience. I have enjoyed and tried every thing from water to coffee to vodka with everything in between. I like to smoke cigars with a brown grain-based spirit. That could be Scotch, Irish whiskey, Bourbon or Corn whiskey. I am also very fond of good quality Rums with cigars; the darker the rum the better. Beers are good with cigars but often lose themselves in the complexity of the cigar unless they themselves are also intensely flavored and can stand up to the cigar. In this regard I like Stouts when smoking a cigar.
I like to enjoy cigars after a good meal. Cigars seem to compliment a meal heavy in proteins that Americans enjoy. Beef, Turkey, Pork and most game go excellent with an after supper cigar. Most fish, with the exception of the red fleshed fishes seem to suffer with a cigar after supper and the same can be said of delicate dishes made from chicken, salads, and other light fodder. To settle down, after a good supper with a good cigar is one of those memorable moments that stick with a man.
I like bargain cigars. I have found that I can find cigars to suit my tastes usually around $5 a stick or less. Yeah, I have smoked some expensive cigars in my times, and they were fine, but I am not sure they were worth $25, $30 or more. The cigars I smoke most often are either Padron's or La Gloria Cubana seconds. There are plenty of cigars for well under $5 a piece that are superb.