Depends on what flavor profiles you like. I started on Hoyo de Monterey Excaliburs back in the 90s. I found them easy to get along with. Big dark cigars are liable to knock you on your butt. You'll swear you just smoked a big, fat joint. You may want to steer clear of those, in the beginning. I have a full humidor, but have smoked in a few years. Just kind of fell out of the habit.
At any rate, Padrons are nice. La Gloria Cubana I liked. There are so many to choose from. Best advice, if you can get to a local brick and mortar cigar store; get friendly with the people that work there. They are usually very patient, and provide good advice and direction.
Relaxing is a good way to describe it. A cigar and a glass of scotch, bourbon or a Stout/dark beer is a wonderful way to spend an hour!