As of right now I am the reigning King of Cuban cigar and Japanese whiskey pairings because as I have done it more than most. Here are the following; Yamazaki paired with Bolivar, Namakubi paired with Hakushu, Hoyo de Monterrey paired with Hibiki 12, and now Partagas 2014 Edicion Limitada (not to mention the other Japanese whisky and non-Cuban cigar pairings). Why do I love pairing Cubans with Japanese whisky? The answer is simple, terroir.
Terroir is everything if you understand that flavors should have a home while so many flavors are completely homeless (go to your local tobacconist and you can easily observe the traffic going to the flavored cigar humidor and as patrons open bottles of peach pie flavored whiskey). Cuban cigars are a direct result of Cuba which is special due to its volcanic soil, elevation, sun exposure, people, and water content. The Japanese whisky has the advantage of meticulous manufacturing which is a hallmark of Japanese culture, the water streams used by the Japanese distilleries are protected by the government, and the Mizunara oak barrels used to age the whiskey. Together it's enough distinctive flavor to please me but it's more than that.