One of the most important tips I can give a cigar smoker who has to smoke where it’s cold is- When smoking where the temperature is less than 50 degrees, keep the cigar warm until you’re ready to cut and light the cigar. If you’re standing around before you’re ready to light up, keep the cigar in an inside pocket, or hold it in your hand. If you allow the cigar to get down to the temperature of the outside air, the disparity in the temperatures may cause the cigar to crack and bloom like an orchid. It’s also far better to cut the cigar indoors where it’s warm to reduce the chance of shattering the cap.
If you’re using a butane lighter to light up, especially if it’s a torch-type, keep the lighter warm (in an inside or pants pocket, or held in the hand). The problem is that, for a butane torch to ignite, the gas must be warm enough to convert from a liquid to a gaseous form when the valve is open. Keeping the lighter as close as possible to body temperature will help assure that your torch will work.
To take the idea a step further, consider the possibility of using a liquid-fuel (Zippo-type) lighter. Of course, the big knock on these lighters is the taste and smell of the fuel. This used to be an undeniable fact, because the fuel was made of naphthalene (also used as a spot remover for clothing) which has a noticeable chemical odor. But in the past few years, this is no longer a big issue, as Zippo has developed a new fuel based on an extract of paraffin, and is virtually odorless and tasteless. I still detect a bit of an odor and an almost imperceptible flavor from it, but it doesn’t last much beyond the first puff or two. They will light easily when it’s cooler, and they’re as close to windproof as a lighter can get.
Also, if you have a garage man-cave that’s heated with a kerosene heater or something similar, don’t store the cigars in the area. The lingering odor of the fuel or from any other source (stored paint, etc.) can easily contaminate the tobacco.