The 25 Best Cigars of the Year 2008
H. Upmann Sir Winston
Large cigars have gone almost completely out of fashion. It’s not that their quality has diminished: they still deliver loads of flavor with a cool, refined character. The problem is that few people have the time to smoke such a large cigar as the Sir Winston—let alone such longer ones as double coronas. But aficionados who do opt for a large cigar usually puff on a Romeo y Julieta Churchill or a Cohiba Esplendido. Perhaps that’s why Cuba makes so few Sir Winstons, most of which are rolled in the new H. Upmann factory on the outskirts of Havana. Until the mid-1990s, the cigar came in a smart green lacquered box, but today it comes in a varnished cedar one with a clasp. The band, once the standard brown and white H. Upmann, is now gold, white and red.
Find some time if you are going to smoke this. It’s worth relaxing and contemplating what the Sir Winston has to offer. It’s so good to look at that you may not want to see it go up in smoke. The ones we smoked had beautiful silky, oily wrappers and excellent caps. The first puffs were immediately rich with leather and spice, then developed into woody, meaty undertones. This cigar has the richness and structure to age well. We think that Winston Churchill would have loved this cigar.