If practicality is the goal, planning is the answer. Where? Who / who else? How long? Let's answer these one at a time.
Where?: Well…this one may just lead to more questions, so let’s define it a little more succinctly. At your destination, where exactly will you smoke? Will there be multiple opportunities at the same spot or are you just hoping to find a spot? If you’re not sure what accommodations are available, you’d do well to call ahead to find out. Many places that accommodate cigar smoking allow you to bring your own, but if they do sell them there, it’s a reasonable courtesy to buy at least one from your host. It’s a good idea to consider this for each time you visit this venue.
Who/who else?: Will you be enjoying cigars alone or with others? Will they bring their own or should you plan to provide the cigars? Of course how you answer these helps further define the number of cigars you’ll need to have on hand. Speaking for myself, I know there are some people I see routinely whose expectation is always that I’ll have one for them, too…and I’m always happy to oblige.
How Long?: This is the easy one…but it’s worth considering. How many days, how many cigar sessions per day, how long is each session, and of course, the multiplier for who/who else.
Bottom line, it’s better to have too many than not enough. If 3 is enough, take 5. If 5 is enough, take 8. And if you need someone to burn one with, just give me a call. I’m here for ya. :)
PS: If your humidor won't hold more than 8, I have a solution for that, too...
—Danny Jackson