I have two traveldors. One holds between 5-8 cigars, the other can hold between 12-15. I pack them both full of different sizes and marques and let the situation dictate what I'll smoke.
However, I don't regularly smoke large cigars (DCs, Churchills, etc) so I usually pack 2-3 of those since I figure if I'm on vacation, I might have some extra spare time to enjoy these larger ones.