For the best man, get a Punch, H. Upmann, and a Romeo y Julieta. Buy them at a local cigar shop and make sure you get a size that fits in the case.

As for the rest of the cigars, just buy two 5-packs of Macanudos, again a size that will fit in the cases. Macanudos are typically mild and can be enjoyed by a new smoker or an older one.