If you don't have a personal humidor and need to keep a cigar for a few days before you smoke it, I suggest going with a 'tubed' cigar; it will stay properly humidified in its tube for a week or so. Or you can opt for a seal-type Baggie and put a couple of Water-Pak or other humidifying devices inside it with your smokes.
I also suggest you go with the larger ring-gauge cigars, typically a 50 or 60 (the larger the number, the bigger the diameter of the cigar). They sustain a burn easier and are generally much less harsh. Make sure you get a good cutter and learn how to cut the right amount from the end, it is important for a good burn.
I've been smoking CAIN brand cigars for some time and they are always, ALWAYS a good smoke. Good draw, nice and even smoke, good 'finish'. I like the Nub version, in a Maduro wrapper. This is just a shorter version of their robusto, and gives you about a 30 minute experience.
The My Father line of cigars is another that tends to have good construction and a reliable burn. There is nothing more frustrating with trying to smoke a cigar than not being able to draw it properly, or having to relight it constantly. These My Father smokes, along with their other Jose Garcia line of products, are nice and consistent.
A newcomer to my humidor has been the Flor De Las Antillas Belicoso cigar (long name, huh?). So far I've been very happy with them. They seem to be much like one of my all-time favorites, Le Flor Dominicana...which are hard to get right now for some reason.
As for Cuban cigars, real ones are hard to get though not impossible. However, don't be fooled by the "mystique" of the Cuban, these days the offerings from Nicaragua, Honduras, Jamaica, and the Dominican Republic are essentially just as good. In fact, most of the families that had Cuban cigar factories fled Cuba and established their name-brand cigars in these other countries, using the same seed they had in Cuba, and nearly identical growing conditions. I know fellow smokers who consider themselves "connoisseurs" because they insist on smoking only Cubans. For the most part these guys are posers that couldn't tell a $10 cigar from a $500 cigar. There are some really rare Cubans out there that sell for thousands of dollars per cigar, but that also means there are a lot of fake versions of these smokes, too. Don't get me wrong, I've smoked a few Cubans that I literally used a roach-clip on, and smoked to about 3/8" in length...that were so good they must have been rolled on the smooth thighs of angels, but even those I didn't pay more than $25 for. And they are sometimes inconsistent, so you go thru the hassle of getting these things only to be disappointed sometimes.
Hope this gives you some ideas, a fine cigar can be a really nice experience. The stronger ones will give you a marijuana-like "high", and if you enjoy whiskey, brandy, or Cognac...there are a lot of cigars that compliment these drinks for an even more enjoyable experience.