H. Upmann Gran Reserva Sir Winston 2011

Description

Only 5,000 numbered black lacquer boxes exist in the world. The H. Upmann Sir Winston Gran Reserva Cosecha 2011 represents the pinnacle of Cuban cigar making—tobacco harvested from the 2011 crop, aged a minimum of five years before rolling, then presented in museum-quality packaging. Unveiled at the Festival del Habano XIX in 2017 and released in 2018, this limited edition transforms the already legendary Sir Winston into something approaching art. At roughly $100 per cigar at launch, this isn’t a smoke—it’s a statement.

The Smoking Experience

First Third: The Gran Reserva announces its pedigree from the cold draw: sweet orange peel, creamy milk chocolate, cinnamon, leather, and cedar intertwine with remarkable clarity. Once lit, the profile is insanely complex—layer upon layer of distinct flavors revealing themselves with each draw. Caramel candy sweetness emerges alongside cranberry brightness. The five years of aging have married these elements into something seamlessly integrated. The smoke is luxuriously smooth, maintaining a deliciously clean and mellow character that belies its depth.

Mid-Section: The heart of this Churchill showcases why Gran Reserva commands its premium. Leather and pepper provide structure while marzipan sweetness softens the blend. Chocolate evolves from milk to something richer—cocoa nibs, dark and sophisticated. Pecan and baking spices add warmth. The orange peel note persists, threading through the profile like a signature. Some draws bring unexpected peanut butter richness. The body remains firmly in the mild-to-medium category despite the complexity—proof that intensity and depth are different things entirely.

Final Third: The conclusion maintains the cigar’s refined character. The flavor palette remains remarkably clean, each element distinct yet harmonized. Coffee notes strengthen—ground espresso joining the chocolate foundation. Cedar and hay assert themselves as the smoke intensifies. The burn remains perfect throughout, the draw effortless. The five-year aging process has eliminated any harshness that might plague younger tobacco; this cigar simply doesn’t turn bitter. What began as exceptional ends as memorable.

Flavor Profile

The Gran Reserva Promise

Habanos S.A. introduced the Gran Reserva designation in 2009 to crown their absolute finest production. The requirements are exacting: all tobacco—wrapper, binder, and filler—must be aged a minimum of five years before rolling. Only selected vitolas from the most prestigious marcas qualify. The H. Upmann Sir Winston, already revered as one of Cuba’s finest Churchills, receives the Gran Reserva treatment with the 2011 harvest. The black lacquer boxes with gold embossing, the numbered certificates, the velvet sleeves—these aren’t mere marketing. They’re acknowledgment that what’s inside represents Cuban tobacco at its theoretical maximum.

Perfect Pairings

• Cognac: XO or hors d’âge—this cigar justifies your finest brandy. The orange and chocolate notes find their match in aged grape spirit.
• Single Malt: Speyside, 18+ years—Glenfiddich 21 or Macallan 18. Sherry cask influence complements the dried fruit notes.
• Rum: The rarest añejos—Havana Club Máximo or Dictador 20 Years. Match excellence with excellence.
• Port: Vintage port from an exceptional year. The cigar’s complexity deserves wine with equal depth.

Ideal For

The H. Upmann Sir Winston Gran Reserva Cosecha 2011 is for collectors, for milestone celebrations, for moments that demand something beyond ordinary excellence. This isn’t your Tuesday evening cigar—it’s the birth of a child, the closing of a career-defining deal, the wedding anniversary measured in decades. At ninety minutes of smoking time, you’re not just consuming tobacco; you’re participating in Cuban history. The 2011 harvest, the five-year aging, the limited 5,000-box production run—every element conspires toward a singular experience. If you own a box, you own something irreplaceable. If you’re considering purchase, understand that you’re buying more than cigars; you’re acquiring artifacts that will only become rarer as years pass.

Investment Note: Gran Reserva releases consistently appreciate in value. The 2011 Sir Winston, with its limited production and impeccable reputation, represents both smoking pleasure and tangible investment. Store properly and you hold something that gains worth while it ages to even greater perfection.