H. Upmann Sir Winston

$ 1,010.00

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9.6 uit 73.482 reviews


Cedar Box of 25,  7 x 47,

Rated 92 Cigar Aficionado: Feb 01, 2023

The H. Upmann Sir Winston is an iconic cigar and one of the most prestigious within the H. Upmann brand, renowned for its long tradition and excellence in crafting Cuban cigars. Named in honor of Sir Winston Churchill, a well-known aficionado of habanos, it stands out for its large Julieta No. 2 format, offering a rich and complex smoking experience, making it a favorite among connoisseurs worldwide.

Features and Flavor Profile

The H. Upmann Sir Winston is characterized by a length of 178 mm (7″) and a ring gauge of 47, classifying it among the larger cigars. This vitola allows for a slow and pleasurable evolution of flavors, providing the smoker with an immersive and extended experience. The tobaccos selected for this cigar come from the Vuelta Abajo region, known for producing the world’s finest tobacco, thus ensuring the highest quality and consistency in each cigar.

The flavor profile of the H. Upmann Sir Winston is notably balanced and sophisticated, offering notes of cedar, cream, and nut, complemented by subtle touches of spices and a sweet undertone. The smoke is medium-bodied, making it accessible and enjoyable for both novice aficionados and the most experienced palates.

Smoking Experience

Smoking an H. Upmann Sir Winston is a truly luxurious experience, ideal for moments of reflection or to accompany special celebrations. Its flawless construction ensures an even burn and excellent draw, allowing the flavors and aromas to fully express themselves. The richness and complexity of its profile make it an excellent choice to be enjoyed alone or paired with a fine spirit, such as a cognac or a single malt.

Recognition and Prestige

The H. Upmann Sir Winston has been celebrated by aficionados and critics alike, establishing itself as one of the most emblematic and respected cigars within the H. Upmann brand. Its prestige is derived not only from the exceptional quality of the cigar but also from its association with Sir Winston Churchill, adding an aura of history and distinction to each smoke.


The H. Upmann Sir Winston is more than just a cigar; it is a masterpiece of Cuban cigar craftsmanship, encapsulating tradition, art, and a passion for fine tobacco. It offers an unforgettable smoking experience, marked by elegance, balance, and depth of flavor. For collectors and aficionados seeking the best of the best in the cigar world, the H. Upmann Sir Winston represents an exceptional choice, symbolizing the pinnacle of quality and luxury in the art of smoking.


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