If you turn to “cigar etiquette” sources, you might have heard you should never smoke more than half a cigar (downright ridiculous, if you ask me). Another common “rule” is that you should set your cigar down and let it burn itself out (not snuff it out) when three finger-widths are left, measured from the end.
Of course, that really only matters if you are smoking in the company of people who care more about arbitrary and rather questionable rules on etiquette than they do about reaping all the enjoyment they can out of a good stogie. You pay a lot for your cigars, so you should be able to enjoy them to their fullest.
There really are no hard-and-fast rules on how far down you can smoke your cigar. A lot of it depends on the cigar in question, as well as your personal tastes. Some cigars get hot and harsh well before you reach the nub. Some of those cigars you might very well want to abandon before you get even halfway. Others taste great right to the very end, and with those, you may very well decide it’s worth the risk of burning your fingers to take it down to the nub. With time and experience, you’ll know which cigars you’re likely to be able to burn down all the way.
If pain isn’t your thing and you’d rather not burn your fingers, there’s a handy device you can purchase for less than $15 called the Havana Saver Cigar Tool. When you’re getting down toward the nub, you can insert the Havana Saver into your cigar and use it to hold your stogie. It doubles as a cigar holder at the golf course and a draw poke, and it’s highly rated by customers.