I got into smoking cigars last summer and I've spent a ton of time since then researching and tasting.
What I love most is the 45 minutes alone with my thoughts or in a lively discussion with a friend.
Its a form of meditation for me.
If you're interested, heres what I know:
The best time to smoke a cigar is while reading or writing for me.
It gets the creative juices flowing.
Make sure to eat beforehand and drink water (or soda) to avoid tobacco sickness early on, or pair with a great bourbon or scotch on a weekend evening.
It's not very expensive unless you want it to be.
You can find amazing $5 cigars online with free shipping.
I use cigarpage dot com and my favorite "starter cigar" is H. Upmann's Vintage Cameroon or the Perdomo Reserve Champaign. Light, smooth, intricate, burns great, and $5-7.