What to drink alongside
The useful principle is simple: match intensity first, then look for a flavour in common. Get the intensity wrong and nothing else matters.
A cigar and a drink are competing for the same palate. If one is much stronger than the other, you stop tasting the weaker one within a few minutes — which is why a delicate Dominican and a cask-strength whisky is a waste of both. Start by matching weight. Only then think about whether the flavours share anything.
What follows is organised by where the tobacco was grown, because origin predicts intensity better than brand does.
Cuba
Aged rum, or a Grande Champagne cognac
Cuban blends tend towards cedar, coffee and a dry earthiness rather than sweetness. An aged rum meets that with its own barrel character without adding sugar to the smoke; cognac does the same with more fruit behind it.
Less successful: Heavily peated whisky, which buries the tobacco rather than meeting it.
Nicaragua
Islay single malt, or cask-strength bourbon
Nicaraguan tobacco is the most assertive we stock — pepper, dark cocoa, real strength. It is the one origin that will not be flattened by a peated whisky, and the smoke and the spirit end up trading intensity.
Less successful: Anything delicate. A light white wine simply disappears.
Dominican Republic
Speyside malt, vintage champagne, or a cortado
Dominican blends are the smoothest of the three big origins — cream, almond, light spice. They suit a drink that stays out of the way, and they are the ones that genuinely work before dinner rather than after.
Less successful: Cask-strength spirits, which will overrun them.
Honduras
Tawny port, or rye
Honduran leaf sits between Cuban earthiness and Nicaraguan pepper. Port picks up the cocoa in it; rye picks up the spice.
Coffee, and the time of day
Espresso works with almost anything on this list, and it is the one pairing that suits a cigar in the morning. A longer, milkier coffee suits the lighter Dominican blends and gets lost against a Nicaraguan.
Worth saying plainly: none of this is a rule. If you like a particular cigar with a particular drink, that is the correct pairing. The reasoning above is a starting point for people who would rather not guess with a CHF 50 cigar.