I enjoy a good cigar, but am in general a non-smoker. We used to smoke 1-3 cigars an evening in our favorite american cocktail bar when it was still allowed to smoke inside in Europe. Don't get me wrong - personally I'm a fan of banning smoking in restaurants/bars, I just miss it in my bar.
They had the perfect interior - dark wooded furniture, comfty chairs, walls lined with whisky bottles and played classics like Sinatra all evening. Paired with a very humorous british waiter and a great mixer it was the perfect setup.
As for cigars I started out by being offered a "Moods" by a friend - defenitely not a quality cigar I'd say, but I got interested and explored the possibilities a bit. Nowadays I prefer light cigars from a manufactory in Germany (Taks recommendation, thank you pal) and for celebrations a Bossner Ambassador. Light cigars are perfect as a very occasional smoker. (The last time I had a Montechristo Edmundo from a pal I had a 2 hour nicotine shock)
From time to time I attended tasting held by the store where we acquired the cigars most of the time, they had interesting presentations by manufactors, including classic companies like Davidoff for the newest Avo Line, but also brands like Total Flame.
Since the ban in restaurants and bars I smoke the most when I'm fishing. There's nothing like setting up your folding chair, opening a beer, lighting a cigar and hoping the damn fish won't interrupt your perfect moment.
