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$250+

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.

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  • Davidoff Winston Churchill Churchill Box Closed Davidoff Winston Churchill Churchill 4-Pack

    Davidoff Cigars

    Davidoff Winston Churchill Churchill

    $27.80 - $556.00

    The Davidoff Winston Churchill Churchill is a commanding expression of excellence—crafted to embody the complexity, charisma, and uncompromising character of the man for whom it’s named. Measuring a stately 6 7/8" x 47, this vitola offers a...

  • Davidoff Winston Churchill The Late Hour Churchill Box Open Davidoff Winston Churchill The Late Hour Churchill 4-Pack

    Davidoff Cigars

    Davidoff Winston Churchill The Late Hour Churchill

    $31.20 - $624.00

    The Davidoff Winston Churchill The Late Hour Churchill captures the essence of the man who led with resolve when the world was at its darkest. This commanding 7" x 48 cigar is a tribute to the late hours Sir Winston Churchill kept—when his most...

  • Davidoff Maduro Short Corona Box Closed Davidoff Maduro Short Corona Single Cigar

    Davidoff Cigars

    Davidoff Maduro Short Corona

    $43.00 - $860.00

    Don’t let its size fool you—the Davidoff Maduro Short Corona delivers a full-flavored, luxurious experience in a refined, compact format. Measuring just 3 3/4" x 46, this cigar is ideal for those who demand rich complexity in a shorter moment...

  • Davidoff Colorado Double R Box Open Davidoff Colorado Double R Single Cigar

    Davidoff Cigars

    Davidoff Colorado Claro Double R

    $49.80 - $498.00

    The Davidoff Colorado Claro Double R is a rare and distinguished cigar that delivers a long, elegant smoking experience for those who seek complexity without compromise. Measuring an impressive 7 1/2" x 50, this Double Corona format showcases the full...

  • Davidoff Maduro Toro Box Closed Davidoff Maduro Toro Single Cigar

    Davidoff Cigars

    Davidoff Maduro Toro

    $54.00 - $1,080.00

    The Davidoff Maduro Toro is a luxurious interpretation of boldness and balance—crafted for those who seek depth without compromise. Measuring 6" x 54, this full-bodied cigar elevates the Maduro experience through precision aging, expert blending,...

  • Davidoff Colorado Claro Aniversario No 3 Box Open Davidoff Colorado Claro Aniversario No 3 Single Cigar

    Davidoff Cigars

    Davidoff Colorado Claro Aniversario No 3

    $37.20 - $372.00

    The Davidoff Colorado Claro Aniversario No. 3 is a sophisticated Toro-sized cigar that unites elegance, balance, and bold flavor in a format designed for refined indulgence. Measuring 6" x 50, this rare expression features Davidoff’s highly coveted...

  • Davidoff Winston Churchill Petit Corona Box Closed Davidoff Winston Churchill Petit Corona 5-Pack

    Davidoff Cigars

    Davidoff Winston Churchill Petit Corona

    $15.90 - $318.00

    The Davidoff Winston Churchill Petit Corona (4" x 40) offers a rich, medium-bodied smoking experience in a smaller format. Handcrafted in the Dominican Republic, this cigar features a blend of aged Dominican fillers and an Ecuadorian Habano wrapper...

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    Davidoff Year of the Snake 2025 Limited Edition Box Closed Davidoff Year of the Snake 2025 Limited Edition Single Cigar

    Davidoff Cigars

    Davidoff Year of the Snake 2025 Limited Edition

    $620.00

    The Davidoff Year of the Snake 2025 Limited Edition is a luxurious 7" x 43 Lancero masterpiece crafted to honor the wisdom, complexity, and grace of the Chinese zodiac’s most enigmatic sign. This ultra-limited release is part of Davidoff’s...

  • Camacho Toro Selection Fresh Pack

    Camacho Cigars

    Camacho Toro Selection Fresh Pack

    $39.00

    The Camacho Toro Selection Fresh Pack offers a medium-to-full-bodied smoking experience with a blend of bold and complex flavors. Featuring a 6" x 50 Toro size, this selection includes Camacho cigars known for their rich, full flavors and premium...

  • Byron Seleccion Privada No 2 Single Cigar Byron Seleccion Privada No 2 Box Open

    Byron Cigars

    Byron Seleccion Privada No 2

    $50.00 - $1,250.00

    The Byron Seleccion Privada No 2 (5.5" x 54) offers a rich, full-bodied smoking experience with a complex and refined flavor profile. Handcrafted in Nicaragua, this cigar features a blend of aged Nicaraguan and Honduran fillers, wrapped in a luxurious...

  • Bandolero Clandestinos Soberbios Box Open Bandolero Clandestinos Soberbios Single Cigar

    Bandolero Cigars

    Bandolero Clandestinos Soberbios

    $17.50 - $437.50

    The Bandolero Clandestinos Soberbios (5.5" x 54) offers an exceptional smoking experience with a complex and medium-to-full-bodied profile. Handcrafted in the Dominican Republic, this cigar features a premium blend of aged Dominican fillers and a...

  • AVO Syncro Caribe Special Toro Box Open AVO Syncro Caribe Special Toro Single Cigar

    AVO Cigars

    AVO Syncro Caribe Special Toro

    $15.90 - $318.00

    The AVO Syncro Caribe Special Toro (6 x 60) is a masterfully blended cigar that embodies the rich vibrancy of the Caribbean. Wrapped in a flawless Ecuadorian Connecticut wrapper over a carefully aged blend of Dominican and Nicaraguan tobaccos, this...