The traditional drink with cigars is Rum, but since most Rum is consumed as “Light,” “Spiced,” or “Flavored” Rum, it’s insufficient to simply say “Rum.” A good-quality aged rum or Ron Añejo is preferable, something not flavored, spiced, or colored with caramel. Ron Zacapa is an excellent choice, as is Zafra. They pair well with nearly any cigar, but a medium- to medium-full-bodied cigar will stand up nicely to a quality aged Rum.
Another traditional option is Brandy or Cognac, particularly in the English tradition. Winston Churchill is reputed to have drunk Hine Cognac nearly as much as or more than he smoked his signature cigars. Nearly any XO Cognac is great, though you could spend a lifetime and a fortune trying them all. If you prefer to keep it simple, Hennessy XO is phenomenal, and Remy XO is quite good as well. And Mr. Churchill’s Hine is an excellent choice, quite affordable in the VSOP and positively delightful in the XO. Pair them with milder cigars; Connecticut Shade-wrapped mild- to medium-bodied cigars often have a highly nuanced palate of flavors, which can easily be overpowered by fuller-bodied spirits. The subtle flavors and smooth textures of premium Cognac work nicely with lighter cigars.
In the modern context, many cigar smokers prefer Whiskey, predominately Bourbon or Scotch. And with good reason. A full-bodied Bourbon or bold, smokey Scotch are a great pair with rich, tangy maduro or an earthy, spicy Habano. But some of the finest Whiskeys in the world are single-malt Scotches, full of subtlety and balance, which pair quite well with milder cigars. With all its diversity, it’s no wonder Whiskey has taken a leading roll in cigar pairing for contemporary cigar lovers.
One of the most overlooked beverages to pair with cigars is premium aged Tequila. Don Julio Añejo has a rich, buttery flavor, and a refined texture that is about as far from the Tequila of your college days as you can get. It pairs wonderfully with an Arturo Fuente Hemingway or Hoyo de Monterrey.