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+

  • Aging Room Quattro Nicaragua Sonata Maestro 20 Box Open Aging Room Quattro Nicaragua Sonata Maestro 20 Box Closed

    Aging Room Cigars

    Aging Room Quattro Nicaragua Sonata Maestro

    $14.95 - $299.00

    The Aging Room Quattro Nicaragua Maestro is a standout 6" x 52 box-pressed Torpedo that helped earn the Quattro Nicaragua line its title as #1 Cigar of the Year by Cigar Aficionado in 2019. Expertly blended by Rafael Nodal and handcrafted at AJ...

  • Padrón 1964 Anniversary Torpedo & Woodford Reserve Double Oaked Bundle Woodford Reserve Double Oaked Bourbon

    Padron Cigars

    Padrón 1964 Anniversary Torpedo & Woodford Reserve Double Oaked

    $513.00

    The Padrón 1964 Anniversary Torpedo & Woodford Reserve Double Oaked bundle marks the opening chapter of the Padrón Pairing Series, a curated ritual designed to showcase how top-rated Padrón cigars interact with thoughtfully...

  • Trinidad Espiritu Series No. 3 Belicoso Box Open Trinidad Espiritu Series No. 3 Belicoso Box Closed

    Trinidad Cigars

    Trinidad Espiritu Series No. 3 Belicoso

    $13.19 - $263.80

    The Trinidad Espiritu Series No. 3 Belicoso is a bold, full-bodied cigar that highlights the richness of a Mexican San Andrés wrapper in a 6 1/8" x 52 tapered vitola. Blended by AJ Fernandez, this third installment in the Espiritu series...

  • Trinidad Espiritu Series No. 2 Belicoso Box Open Trinidad Espiritu Series No. 2 Belicoso Box Closed

    Trinidad Cigars

    Trinidad Espiritu Series No. 2 Belicoso

    $13.44 - $268.80

    The Trinidad Espiritu Series No. 2 Belicoso offers a vibrant, full-bodied smoking experience that blends Brazilian soul with Nicaraguan strength. Expertly crafted by AJ Fernandez, this 6 1/8" x 52 Belicoso features a tapered head that enhances draw...

  • Trinidad Espiritu Series No. 1 Belicoso Box Open Trinidad Espiritu Series No. 1 Belicoso Box Closed

    Trinidad Cigars

    Trinidad Espiritu Series No. 1 Belicoso

    $13.84 - $276.80

    The Trinidad Espiritu Series No. 1 Belicoso brings together rich Nicaraguan flavor and classic Cuban-inspired design in a striking 6 1/8" x 52 tapered format. Expertly crafted by AJ Fernandez, this Belicoso showcases the bold character of the Espiritu...

  • Montecristo White No. 2 Box Open Montecristo White No. 2 Single Cigar

    Montecristo Cigars

    Montecristo White No. 2

    $21.37 - $576.99

    The Montecristo White Series No. 2 is a 6 1/8" x 52 torpedo that blends timeless Montecristo tradition with smooth, mellow sophistication. Handcrafted in the Dominican Republic, this iconic vitola features a flawless Ecuadorian Connecticut...

  • Montecristo M No 2 Torpedo Box of 20 cigars made in Nicaragua Montecristo M No 2 Torpedo Single Cigar

    Montecristo Cigars

    Montecristo M No 2

    $34.76 - $695.20

    The Montecristo M No. 2 is a striking Torpedo-shaped cigar that delivers a bold and modern interpretation of the Montecristo tradition. Handcrafted by AJ Fernandez in Nicaragua, this 6 1/4 x 52 vitola captures the rich intensity of Nicaraguan tobacco...

  • Padron 1926 Serie 40th Anniversary Maduro Chest of 40 Cigars Padrón 1926 Serie 40th Anniversary Maduro Chest of 40 Single Cigar

    Padron Cigars

    Padron 1926 Serie 40th Anniversary Natural Chest of 40

    $2,106.00

    The Padrón 1926 Serie 40th Anniversary Natural Chest of 40 is a landmark celebration of tradition, craftsmanship, and prestige, crafted for the true cigar connoisseur. Handmade in Nicaragua from Padrón’s oldest and most select...

  • Padron 1926 Serie 40th Anniversary Maduro Chest of 40 Cigars Padrón 1926 Serie 40th Anniversary Maduro Chest of 40 Single Cigar

    Padron Cigars

    Padron 1926 Serie 40th Anniversary Maduro Chest of 40

    $2,106.00

    The Padrón 1926 Serie 40th Anniversary Maduro Chest of 40 is the ultimate celebration of craftsmanship, heritage, and prestige. Created to honor Padrón’s 40th anniversary, this extraordinary offering features forty meticulously...

  • Padron 1926 Serie 40th Anniversary Maduro Box Open Padron 1926 Serie 40th Anniversary Maduro Single Cigar

    Padron Cigars

    Padron 1926 Serie 40th Anniversary Maduro

    $32.00 - $640.00

    The Padrón 1926 Serie 40th Anniversary Maduro is a legendary cigar crafted to honor four decades of Padrón excellence, delivering an unmatched smoking experience for true connoisseurs. Handmade in Nicaragua with Padrón’s finest...

  • Ferio Tego Timeless Prestige No 2 Torpedo Box Open Ferio Tego Timeless Prestige No 2 Torpedo Single Cigar

    Ferio Tego Cigars

    Ferio Tego Timeless Prestige No 2 Torpedo

    $13.60 - $272.00

    The Ferio Tego Timeless Prestige No. 2 Torpedo is an expertly crafted 6.25 x 52 cigar that delivers a refined, medium-bodied smoking experience. Handcrafted in the Dominican Republic, this premium cigar features a Honduran wrapper over a Dominican binder...

  • El Septimo Sacred Arts Collection Rembrandt Box Open El Septimo Sacred Arts Collection Rembrandt Single Cigar

    El Septimo Cigars

    El Septimo Sacred Arts Collection Rembrandt

    $26.00 - $520.00

    The El Septimo Sacred Arts Collection Rembrandt is a meticulously crafted 7" x 54 Torpedo cigar, paying homage to the renowned artist Rembrandt and inspired by his masterpiece, The Return of the Prodigal Son. This medium-bodied cigar offers a harmonious...