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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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Rare Finds Cigars

Padrón Rare Finds “A Hammer & A Dream” Natural & Maduro Old Elk Bourbon Bundle

MSRP:

Was:

Now: $1,590.00

The Padrón Rare Finds “A Hammer & A Dream” Natural & Maduro Old Elk Bourbon Bundle is the pinnacle of luxury for cigar and bourbon aficionados. This trio includes a full box each of the Padrón Rare Finds Natural and...
Rare Finds Cigars

Padrón Rare Finds “A Hammer & A Dream” Natural Old Elk Bourbon Bundle

MSRP:

Was:

Now: $1,000.00

Celebrate legacy and craftsmanship with the Padrón Rare Finds “A Hammer & A Dream” Natural Old Elk Bourbon Bundle. This limited-edition bundle includes a full box of Padrón Rare Finds Natural cigars—crafted from the...
Rare Finds Cigars

Padrón Rare Finds “A Hammer & A Dream” Maduro Old Elk Bourbon Bundle

MSRP:

Was:

Now: $1,000.00

The Padrón Rare Finds “A Hammer & A Dream” Maduro Old Elk Bourbon Bundle is an exclusive pairing of two masterful expressions—premium aged Nicaraguan cigars and a 10-Year Old Elk bourbon that pays tribute to the legendary...
Rare Finds Cigars

Old Elk 10-Year Single Barrel Bourbon — A Hammer & A Dream: Padrón Edition

MSRP:

Was:

Now: $410.00

The Old Elk 10-Year Single Barrel Bourbon — A Hammer & A Dream: Padrón Edition is a rare and evocative expression crafted for the aficionado who appreciates heritage, boldness, and refinement in equal measure. Bottled at 115.6 proof and...
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Padron Cigars

Vintage Padrón 1964 "A" Natural & Maduro Set (2009)

MSRP:

Was:

Now: $1,300.00

The Vintage Padrón 1964 "A" Natural & Maduro Set (2009) represents a remarkable opportunity to own a piece of cigar history. This collector’s edition pairs two ultra-rare “A” size cigars—one in the rich, full-bodied...
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Padron Cigars

Vintage Padrón 1964 "A" Maduro (2009)

MSRP:

Was:

Now: $700.00

The Vintage Padrón 1964 "A" Maduro (2009) is a majestic showcase of age, rarity, and the Padrón family’s unwavering commitment to excellence. Measuring an impressive 8½ inches in length with a 50-ring gauge, this elegant...
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Padron Cigars

Vintage Padrón 80 Years Natural & Maduro Set (2009)

MSRP:

Was:

Now: $1,200.00

The Vintage Padrón 80 Years Natural & Maduro Set is a tribute to legacy, rarity, and uncompromising craftsmanship—featuring one of the most revered celebratory cigars ever created. Released in 2006 to honor the 80th birthday of...
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Padron Cigars

Vintage Padron Family Reserve 45 Years Maduro (2009)

MSRP:

Was:

Now: $700.00

The Vintage Padrón Family Reserve 45 Years Maduro is a masterpiece of legacy and craftsmanship—an ultra-rare, aged cigar that commemorates the 45th anniversary of the iconic Padrón brand. Originally released in 2009, this special...
Drew Estate Cigars

Undercrown Shade Corona Doble

MSRP:

Was:

Now: $293.75

The Undercrown Shade Corona Doble is a beautifully balanced long-format cigar that brings nuance, complexity, and elegance to the forefront of Drew Estate’s Connecticut-style offerings. Measuring 7 x 54, this cigar provides a cool, extended smoking...
Drew Estate Cigars

Undercrown Shade Gordito

MSRP:

Was:

Now: $311.25

The Undercrown Shade Gordito is a bold take on Drew Estate’s celebrated Connecticut blend—crafted for those who want a longer, richer session without compromising smoothness or balance. Measuring 6 x 60, this hefty vitola showcases the creamy...
Drew Estate Cigars

Undercrown Shade Gran Toro

MSRP:

Was:

Now: $256.25

The Undercrown Shade Gran Toro is a creamy, complex, and elegantly constructed cigar that showcases Drew Estate’s masterful approach to Connecticut-blended craftsmanship. Measuring 6 x 52, this Gran Toro format delivers a balanced, medium-bodied...
Drew Estate Cigars

Undercrown Shade Gran Toro Fresh Pack

MSRP:

Was:

Now: $51.25 - $256.25

MSRP:

The Undercrown Shade Gran Toro Fresh Pack delivers Drew Estate’s signature smooth and complex Connecticut blend in a convenient, humidity-controlled format. Featuring five 6 x 52 Gran Toro cigars sealed in a resealable, travel-ready pouch, this...

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