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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 Toro Box Closed Davidoff Winston Churchill Toro Pack of 4

    Davidoff Cigars

    Davidoff Winston Churchill Toro

    $25.00 - $500.00

    The Davidoff Winston Churchill Toro is a bold, refined cigar that mirrors the complexity and grandeur of its namesake. Measuring 6" x 54, this Toro vitola brings together strength, elegance, and depth—paying tribute to Sir Winston Churchill's...

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    Davidoff Nicaragua 10th Anniversary Box Closed Davidoff Nicaragua 10th Anniversary Box Open

    Davidoff Cigars

    Davidoff Nicaragua 10th Anniversary Limited Edition

    $36.00 - $432.00

    The Davidoff Nicaragua 10th Anniversary is a limited-edition masterpiece that celebrates a decade of daring innovation and Davidoff’s trailblazing success in Nicaragua. This commemorative 6" x 53 Robusto Extra encapsulates the fiery soul of...

  • Davidoff Signature 1000 Box Closed Davidoff Signature 1000 Pack of 4

    Davidoff Cigars

    Davidoff Signature 1000

    $14.60 - $365.00

    The Davidoff Signature 1000 is a masterfully constructed small-format cigar that exemplifies elegance, balance, and subtlety. Measuring 4 5/8" x 34, this timeless classic is part of the renowned Davidoff Signature Series, delivering a refined smoking...

  • Davidoff Grand Cru No 5 Box Closed Davidoff Grand Cru No 5 Pack of 4

    Davidoff Cigars

    Davidoff Grand Cru No 5

    $15.60 - $390.00

    The Davidoff Grand Cru No. 5 is a compact yet sophisticated offering in the Grand Cru Series—crafted for those who appreciate refined flavor in a shorter format. Measuring 4" x 41, this petit corona delivers all the elegance and nuance expected...

  • Davidoff Winston Churchill Robusto Box Closed Davidoff Winston Churchill Robusto Pack of 4

    Davidoff Cigars

    Davidoff Winston Churchill Robusto

    $22.90 - $458.00

    The Davidoff Winston Churchill Robusto is a commanding cigar that mirrors the complexity, charisma, and boldness of the man it honors. Measuring 5 1/4" x 52, this Robusto pays tribute to Sir Winston Churchill’s multifaceted legacy—with a...

  • Davidoff Millennium Toro Box Closed Davidoff Millennium Toro 4-Pack

    Davidoff Cigars

    Davidoff Millennium Toro

    $33.20 - $332.00

    The Davidoff Millennium Toro is a bold expression of balance and intensity—delivering complexity, strength, and refinement in a commanding 6" x 50 vitola. As a standout in the Millennium Blend Series, this cigar is the choice of discerning...

  • Davidoff Royal Release Salomones Box Closed Davidoff Royal Release Salomones Box Open

    Davidoff Cigars

    Davidoff Royal Release Salomones

    $150.00 - $1,500.00

    The Davidoff Royal Release Salomones is an 8 1/4" x 57 perfecto-shaped masterpiece that sets the standard for luxury in the cigar world. Crafted exclusively from tobaccos aged for 10 years and harvested under Davidoff’s "Cosecha Especial" program,...

  • Davidoff Aniversario Special T Box Closed Davidoff Aniversario Special T Pack of 4

    Davidoff Cigars

    Davidoff Aniversario Special T

    $31.30 - $626.00

    The Davidoff Aniversario Special T is a masterclass in form, flavor, and finesse—celebrated for its elegant torpedo shape and remarkable complexity. Measuring 6" x 52, this tapered beauty allows aficionados to control the draw and evolve the...

  • Davidoff Royal Release Robusto Box Closed Davidoff Royal Release Robusto Box Open

    Davidoff Cigars

    Davidoff Royal Release Robusto

    $120.00 - $1,200.00

    The Davidoff Royal Release Robusto represents the highest expression of cigar-making artistry from one of the world’s most revered luxury houses. Crafted at the exclusive Davidoff atelier in the Dominican Republic, this masterpiece is hand-rolled...

  • Davidoff Millennium Short Robusto Box Closed Davidoff Millennium Short Robusto Pack of 4

    Davidoff Cigars

    Davidoff Millennium Short Robusto

    $25.10 - $502.00

    The Davidoff Millennium Short Robusto is a bold and beautifully concentrated expression of the celebrated Millennium Blend Series, crafted for aficionados who desire full-bodied flavor in a shorter format. Measuring 4 1/4" x 52, this cigar offers the...

  • Davidoff Grand Cru No 2 Box Closed Davidoff Grand Cru No 2 Pack of 4

    Davidoff Cigars

    Davidoff Grand Cru No 2

    $22.60 - $565.00

    The Davidoff Grand Cru No. 2 is a cigar of impeccable balance and subtle complexity—crafted for the true connoisseur who appreciates refinement in every detail. Measuring 5 5/8" x 43 in a traditional Corona format, this mild-to-medium-bodied cigar...

  • Davidoff Aniversario Special R Tubo Box Open Davidoff Aniversario Special R Tubo Pack of 4

    Davidoff Cigars

    Davidoff Aniversario Special R Tubo

    $27.40 - $548.00

    The Davidoff Aniversario Special R Tubos is an ideal companion for life’s finest moments—delivering the elegance and balance of the Aniversario Series in a refined, travel-ready format. Measuring 4 7/8" x 50, this Robusto cigar is presented...