The Most Expensive Cigar Brands in the World

The most meticulously crafted cigars command suitably hefty price tags. 

Whether enjoyed at home with a glass of whisky, shared with friends at a glitzy European beach club, or savored in a dedicated cigar lounge, the hand-rolled status symbol has long held a place in film, pop culture, and elite travel circles.

A great cigar – flavorsome, balanced, and slow-burning – demands patience and precision. Quality begins with the tobacco leaf, with the world’s best still coming from Cuba. Whole leaves are hand-selected and rolled by skilled torcedors, a process that requires years of training.

While enjoying cigars is rarely an inexpensive pastime, the rarest and most meticulously crafted releases can command extraordinary prices. Below, we explore the most expensive cigar brands in the world, which only produce the best of the best.

The world’s most expensive cigars and brands

Trinidad

One of Cuba’s most exclusive cigar brands, Trinidad has long been associated with special occasions and diplomatic prestige. Established in 1969, the brand was created as a private label for foreign dignitaries visiting Cuba and was not commercially released until 1997.

Trinidad’s cigars are known for their medium body, refined construction, and layered flavor profiles, often marked by earthy, nutty, and subtly sweet notes. Like the finest Cuban cigars, all Trinidads are entirely handmade using filler and binder leaves from the Vuelta Abajo region. Signature details include pigtail caps.

Rare cigars have traded privately and at auction for more than $1,000 per stick, but, until recently, no new conventional release had reached that price point – that is, until the Trinidad Fundadores 55th Anniversary puro. Aged for a decade after rolling and presented in an S.T. Dupont humidor, Trinidad’s triple-banded cigar debuted at $1,150 per cigar, setting a new benchmark for retail Cuban cigars as one of the most expensive cigars in the world.

Gurkha

Founded in 1887, Gurkha is among the oldest cigar brands in the world. After a long hiatus, the brand was revived in 1989 by Kaizad Hansotia, who transformed it into a major force during the modern cigar boom. Today, Gurkha produces cigars across a wide range of price points, but it is best known for its ultra-premium and highly theatrical releases.

Among them is the Maharaja, a limited-edition blend featuring a Maduro wrapper with Dominican binder and filler. Medium-bodied and smooth, it is presented in a 10-count mahogany humidor, complete with individual piano-finish coffins.

Even more extreme is Gurkha’s His Majesty’s Reserve. The blend features a 15-year-old Connecticut Broadleaf Maduro wrapper and a 12-year-aged Dominican binder and filler, infused with a rare cognac once reserved exclusively for dignitaries. 

At the very top of the spectrum sits the Gurkha Royal Courtesan, reportedly sold privately for $1.36 million. Crafted in Honduras and the Dominican Republic, allegedly, the torcedors rolled the cigars blindfolded, to avoid any distraction, with only a few artisans permitted to create the cigars.

The cigar features Himalayan tobacco, gold leaf wrapping, a diamond-studded band, Fiji water–treated leaves, and is infused with Remy Martin’s Black Pearl Louis XIII.

Davidoff

Davidoff is a prestigious Swiss luxury brand, famous for its premium, handcrafted cigars, with the philosophy of ‘Caribbean passion, Swiss precision.’ The brand originates from Zino Davidoff’s family tobacco shop in Geneva, evolving from Cuban roots to current production in the Dominican Republic and Honduras, using diverse New World tobaccos.

The original Oro Blanco Special Reserve 2002 became Davidoff’s rarest cigar at the time, made using exceptionally aged tobaccos and produced in extremely limited quantities. Its success and scarcity led Davidoff to create a successor: the Oro Blanco Special Reserve 111 Years, released in 2024.

Presented in a refined toro format, the cigar is a Dominican puro composed of vintage tobaccos drawn from five distinct terroirs, one of which is no longer cultivated by Davidoff. In total, the blend combines seven tobaccos whose cumulative age reaches an unprecedented 111 years, making it the most tobacco-aged cigar Davidoff has ever produced.

Crafted exclusively by master roller supervisors with a minimum of 20 years’ experience, the cigar is released only once Davidoff’s master blenders agree it has reached peak maturity. The result is a full-bodied yet controlled smoke that evolves steadily throughout.

The Oro Blanco Special Reserve 111 Years is designed for slow, deliberate smoking and remains one of the most expensive and collectible non-Cuban cigars available today.

Cohiba

Cohiba is the flagship brand of Habanos S.A. and is widely regarded as the pinnacle of Cuban cigar production. Created in 1966 exclusively for Fidel Castro, Cohiba cigars were originally rolled at the El Laguito factory and reserved solely for diplomatic gifts. Public sales did not begin until 1982.

The name “Cohiba” comes from the Taíno word for tobacco bundles smoked by indigenous Cubans – an early precursor to the modern cigar.

What sets Cohiba apart is its tobacco selection and fermentation process. Leaves are sourced from the finest Vegas de Primera in San Juan y Martínez and San Luis, within the Vuelta Abajo region. Uniquely, Cohiba subjects up to three filler leaves – seco, ligero, and the rare medio tiempo – to a third fermentation in wooden barrels, contributing to its distinctive aroma and depth of flavor.

The Cohiba Behike line is widely considered the finest standard-production Cuban cigar available today. Originally released in just 100 humidors of 40 cigars, demand quickly outpaced supply. The blend includes the elusive medio tiempo leaf, which grows on only a small percentage of tobacco plants, ensuring perpetual scarcity. The Behike 56, the largest in the range, delivers a smooth yet complex profile with notes of leather, coffee, dried fruit, and subtle spice.