H. Upmann Sir Winston

The H. Upmann Sir Winston opens with a medium-bodied profile, showcasing creamy cedar, mild leather, and delicate floral notes, complemented by hints of toasted almonds and soft spice, creating a refined and approachable start. The retrohale brings gentle white pepper and subtle nutty undertones, enhancing complexity while remaining elegant and balanced. Midway, flavors evolve into smooth caramel, light cocoa, and a touch of honey sweetness, offering a rich, layered texture without overpowering the palate. The final third finishes with lingering notes of toasted oak, soft espresso, and gentle spice, maintaining a polished and sophisticated character throughout.

For more detailed cigar and whisky pairing recommendations, explore our comprehensive guide to finding the perfect match for your smoking experience.

The Cuban wrapper is silky with a medium-brown hue, expertly rolled over Cuban binder and filler tobaccos. The Sir Winston vitola is well-constructed, with a firm, even pack and a flawless draw. The cold draw reveals hints of hay, cedar, and soft spice. Upon lighting, the burn line remains even, while ash forms solid, light-gray columns that hold well, reflecting meticulous Cuban craftsmanship.

The ideal whisky pairing for the H. Upmann Sir Winston is a smooth, lightly peated Scotch or a mellow Irish whiskey, as the subtle spice and creamy cedar notes complement the cigar’s elegant flavor profile.

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This cigar has good aging potential; it can develop more nuanced sweetness and complexity over several years when stored properly.

Overall, the H. Upmann Sir Winston is a classic, refined Cuban Churchill, offering balanced flavors, consistent construction, and a sophisticated smoking experience.