$250+

$250+ Cigars

For those who seek the pinnacle of cigar craftsmanship, rarity, and prestige, cigars priced at $250+ offer an unparalleled smoking experience. These cigars are crafted using the world’s finest tobaccos, often aged for decades, ensuring deep complexity, smoothness, and refinement. Whether you’re indulging in an ultra-premium Padron, savoring the elegance of Davidoff, or experiencing the prestige of Fuente Fuente Opus X, these cigars represent the ultimate in luxury and sophistication.

At The Tobacconist of Greenwich, we offer a carefully curated selection of cigars over $250, ensuring that every aficionado can experience the highest level of craftsmanship and aging perfection. Whether you’re celebrating a special occasion, expanding a private collection, or enjoying the finest cigars in the world, our ultra-premium selection guarantees exceptional quality and exclusivity. Shop now at The Tobacconist of Greenwich and experience the world's finest cigars over $250.

POPULAR IN $250+

Filter results
  • Montecristo 1935 Anniversary Edición Doble Diamante Red Box Open Montecristo 1935 Anniversary Edición Doble Diamante Red Box Closed Angled Cigar

    Montecristo Cigars

    Montecristo 1935 Anniversary Edición Doble Diamante Red

    $150.00 - $1,500.00

    Montecristo 1935 Anniversary Edición Doble Diamante Red — the second expression of the Doble Diamante series, rated 95 by Cigar Aficionado. Inspired by the rarity and brilliance of a red diamond, this exclusive release showcases some of the...

  • My Father La Lealtad Toro Box Open My Father La Lealtad Toro 5-Pack

    My Father Cigars

    My Father La Lealtad Toro

    $12.50 - $250.00

    My Father La Lealtad Toro — where most smokers will meet La Lealtad for the first time. 6" × 54 ring gauge. Ecuadorian Habano Oscuro Rosado wrapper over a double binder of Honduran and Nicaraguan leaf, with Honduran and Nicaraguan long-filler...

  • My Father La Lealtad Torpedo Box-Pressed Box Open My Father La Lealtad Torpedo Box-Pressed 5-Pack of Cigars

    My Father Cigars

    My Father La Lealtad Torpedo Box-Pressed

    $13.00 - $260.00

    My Father La Lealtad Torpedo Box-Pressed — the box-pressed torpedo expression of the García family's second Honduran release. 6½" × 52 ring gauge. Ecuadorian Habano Oscuro Rosado wrapper over a double binder of Honduran and...

  • My Father La Lealtad Toro Gordo Box Open My Father La Lealtad Toro Gordo 5-Pack of Cigars

    My Father Cigars

    My Father La Lealtad Toro Gordo

    $13.50 - $270.00

    My Father La Lealtad Toro Gordo — the large ring gauge expression of the García family's second Honduran release. 6" × 60 ring gauge. Ecuadorian Habano Oscuro Rosado wrapper over a double binder of Honduran and Nicaraguan leaf, with...

  • Undercrown El Tigre Dominicano Gordo Box Open Undercrown El Tigre Dominicano Gordo 5-Pack of Cigars

    Drew Estate Cigars

    Undercrown El Tigre Dominicano Gordo

    $14.50 - $290.00

    Undercrown El Tigre Dominicano Gordo brings the first Dominican filler-forward Undercrown to the bold Gordo format—a 6" × 60 soft box-pressed vitola that showcases the blend's full potential with maximum smoke output and an extended,...

  • Undercrown El Tigre Dominicano Toro Box Closed Undercrown El Tigre Dominicano Toro 5-Pack

    Drew Estate Cigars

    Undercrown El Tigre Dominicano Toro

    $13.00 - $260.00

    Undercrown El Tigre Dominicano Toro brings the first Dominican filler-forward Undercrown to the flagship Toro format—a 6" × 50 soft box-pressed vitola that allows the blend's layered complexity to unfold fully over an extended smoking...

  • The Titans of Tobacco Collection Full Box Set Fuente Opus X Rare Finds — Titans of Tobacco Collection Box Angled

    Rare Finds Cigars

    The Titans of Tobacco Collection Full Box Set

    $3,640.00

    The Titans of Tobacco Collection Full Box Set. Six houses. Six Rare Finds. One complete collection. The Collection This set includes one box of each of the six exclusive Rare Finds releases created for Titans of Tobacco 2026: (1) Padrón Rare Finds...

  • Fuente Opus X Rare Finds — Titans of Tobacco Collection Box Angled Fuente Opus X Rare Finds — Titans of Tobacco Collection Outer Top

    Rare Finds Cigars

    Fuente Opus X Rare Finds — Titans of Tobacco Collection

    $950.00

    Fuente Opus X Rare Finds — Titans of Tobacco Collection. Fuente Fuente Opus X changed everything. When Carlos Fuente Jr. released the first Dominican puro wrapped in sun-grown Rosado leaf in 1995, the industry said it couldn't be done. The tobacco...

  • Padron Rare Finds — Titans of Tobacco Collection Box Angled Open Padron Rare Finds — Titans of Tobacco Collection Box Angled

    Rare Finds Cigars

    Padrón Rare Finds — Titans of Tobacco Collection

    $750.00

    Padrón Rare Finds — Titans of Tobacco Collection. Jorge Padrón represents the future of one of the most respected names in premium cigars. As the second generation of the Padrón family to lead the company, he carries forward a...

  • La Flor Dominicana Rare Finds — Titans of Tobacco Collection Box Open Angled La Flor Dominicana Rare Finds — Titans of Tobacco Collection Box Angled

    Rare Finds Cigars

    La Flor Dominicana Rare Finds — Titans of Tobacco Collection

    $475.00

    The Maverick returns with a new exclusive. La Flor Dominicana Rare Finds — Titans of Tobacco Collection. Litto Gomez has never been afraid to go his own way. When he founded La Flor Dominicana in 1994, he did it with a commitment to bold,...

  • Foundation Cigars Rare Finds — Titans of Tobacco Collection Box Open Angled Foundation Cigars Rare Finds — Titans of Tobacco Collection Box Angled

    Rare Finds Cigars

    Foundation Rare Finds — Titans of Tobacco Collection

    $475.00

    Foundation Rare Finds — Titans of Tobacco Collection. Nick Melillo doesn't follow trends. He sets them. As the founder of Foundation Cigar Company, he has built a reputation for blends that take risks — and deliver on them. The Tabernacle...

  • Kelner Cigars Rare Finds — Titans of Tobacco Collection Box Angled Open Kelner Cigars Rare Finds — Titans of Tobacco Collection Box Angled

    Rare Finds Cigars

    Kelner Rare Finds — Titans of Tobacco Collection

    $540.00

    Kelner Rare Finds — Titans of Tobacco Collection. The Kelner name is synonymous with Dominican cigar excellence. Hendrik "Henke" Kelner is one of the most influential figures in the modern cigar industry — the founder of Tabadom, master...