There’s no wrong answer.
And that’s also not the only question. Where do you smoke? Or maybe the better question is where do you most often GO to smoke? Whether its the local tobacconist or cigar lounge, or a friend’s back porch or fishing dock, or even a beach a few plane ride hours away, there’s an ideal humidor for you. And regardless whether we smoke pipes or cigars (or both!) or where we enjoy them, we all usually want the same thing: options.

So there’s your first consideration.
Even if you only smoke once per day or week or month, you probably vary from one cigar or tobacco selection to the next more often than not. So get one of appropriate size to give you two or three choices for each smoking occasion. Who else will be there? Will they have their own selections? Take enough to share. When you discover something new or exciting, what’s one of the first things you do? You tell someone about it, right? Well, if you’re fellow smoking fiends are anything like mine, about half the conversations start with either, “Have you had ____ yet?” or “You HAVE to try ____!” I don’t know about you, but I find immense pleasure in giving. If you haven’t found the same pleasure, try it again. Chances are it’ll come back to you in spades. Take enough to share, and even if no one takes you up on it, you’ll have more to choose from next time.

Multiply the number of options you want by the number of smoking occasions you’ll have before reloading your humidor, and there you have it: the number of cigars or pipe tobaccos you’ll want to have with you. There are travel humidors available for as few as 1 to 3 cigars or tobaccos, or as many as you’d need for a Transatlantic two week trip. Perhaps the most important consideration is, where will you keep your selections once you return home? Regardless of whether you have a desktop humidor, a Coolerdor, a large cabinet humidor or even a walk-in humidor at home, you’ll want to be sure that your travel humidor can keep some “at-the-ready” for the next time out. On the flip side, if you only smoke on the go, then it’s all the more important that your travel humidor can keep constant ideal conditions for your tobaccos for the long term. Choose a well-crafted selection that matches your style, seals in humidity sufficiently and you’re well on your way.
If you’re still not sure what size to get, err on the side of bigger. I find it’s always better to have more than you need than to not have enough. Cheers!
— Danny Jackson