If I go more than a cigar or two a day (rare lately); I tend to gauge my cigar based upon time, more then taste. If I have an hour or so to smoke one, then I can look a the 7X50. If I am going inside soon, but have time for a quickie, I can get a 'lil CAO, or mac mini or something like that. I can't think of a situation where I am not outdoors all day, where I can just take a cigar anywhere I am going.
Even at sporting events, horse shows, races, or just sightseeing, there is a rare time where a big cigar won't get in the way of what I am doing. I rather keep my smoking to a minimum and have that one or two nice evening smokes when things are slowed down and there is time to enjoy it.