I used to smoke often enough to warrant a humidor, which I still have but it's not set up. Now I may have 2-3 a year on special occasions, trips, etc but I know what I like.
I'm a Macanudo man. Vintage if I can find one, but regular Conn. shade is fine. Don't like Maduro. Usually go for a Hyde Park but sometimes smaller, depending on the occasion. I agree with the conversation with a good friend. Sitting out on the back porch with a cigar and a glass of whiskey. Not much better in the world.
Romeo y Juliettas are also nice and my best friend is partial to an Arturo Fuente Hemingway which is also a nice stick.
Favorite cigar smoking experience was in New Orleans, right on Canal street. Can't remember the name of the shop but they only carried their House brand, but they would help you pick something based on what you liked. At the time (not sure anymore) you could smoke inside. Leather couch sitting inside, but the entire front of the store was wide open french doors open to the street. Sitting there enjoying a smoke, watching the world go by, music drifting in from the French Quarter across the street. That was an incredible night.