Everyone seems to have whiskey covered.

For cigars I buy from JR's Cigars. you can order a sampler, they have them often, say 20 mixed cigars for about $30-40. Honestly most people cannot taste the difference in cigars, like wine, beer or bourbon. The nuances are tough to pick up even for experienced smokers.

The key thing is to buy smooth easy smoking cigars. I like the Nicaraguans, but they are stronger. Dominican and Honduran are generally milder.

Fuentes are great cigars, if you can find them at a reasonable price.