When I was a little boy, every Sunday evening, dad would settle in for a post-dinner cigar smoke. His ritual involved sinking deep into a chair out on the patio. Taking his sweet time, for these were his moments, he’d pull the cigar out of his shirt pocket, hold it to his nose, breathing deep to admire the sweet aromas before inspecting its rough and grainy exterior. He would then clench the cigar tightly in his lips, holding the flame to the tip while spinning it slowly to ensure an even light, clouds of smoke pouring from the corners of his mouth. Although I couldn’t stand the smell at the time, there was something about the whole manly custom that intrigued me then and has continued to do so to this very day.

Settling in with a cigar is a time-trusted practice that happens in all corners of the globe. And just like any other industry, there is a marked difference between those that one can find at the neighborhood shop and the ones tucked in the safes of respected collectors.

Gurkha His Majesty’s Reserve and OpusX Fuente Fuente are among the most expensive and exquisite cigars in the world. While HMR holds the title of world’s most expensive cigar, checking out at a meager $14,000 for a box of 20, some retailers call OpusX, inarguably, the rarest cigar in the world (a box of 32 will run you around $800).

For years, Gurkha has been known as the Rolls-Royce of the cigar industry. At the height of British rule in India, colonial soldiers began to make their own cigars from local tobacco, leading to the founding of the Gurkha brand. While surely a company with a rich, 100-year history, Gurkha has not always been rich. In fact, just 20 years ago, lifelong businessman Kaizad Hansotia purchased the brand during a trip to India for a mere $149 and brought it to the U.S. With a steadfast commitment to the revival of the company, Hansotia turned Gurkha into a multi-million-dollar enterprise. In 1995, Hansotia struck a deal with Miami Cigar Company, and improved the visual aspects of his packaging, putting the cigars in glass tubes instead of plastic wrappers, and the brand took off, quickly becoming the favored cigar of aficionados.

The company’s headline-making flagship, His Majesty’s Reserve, starts with a 15-year Connecticut Maduro wrapper with 12-year-old Dominican binder that covers a secret blend of filler tobaccos from all over the world. Once the cigars are rolled, they undergo a unique infusion process that involves an entire bottle of treasured Rémy Martin Louis XIII cognac. This infusion does not take away from the tobacco flavor of the aged leaves, but rather complements them in a luxurious fashion. Lighting up one of these bad boys is certainly a rare treat; Only 75 boxes will be made this year, down from last year’s 86, and 70 of those boxes have been pre-sold.

The Fuente Fuente OpusX is the premiere cigar line in the legendary Fuente family, whose heritage can be traced to Cuba, where the first cigars bearing the Fuente name were hand-rolled in 1912. In honor of the family history, OpusX is the first successful cigar to be made with a Cuban-seed wrapper grown in the Dominican Republic, on the Fuente plantation, Chateau de la Fuente. The Opus name is derived from this unique silken Rosado wrapper, which gives the cigar its fine and balanced complexity. The cigar is the result of a dedicated collaboration between two generations (Carlos Sr. and Carlos Jr.), hence the double Fuente in the name.

While growing, the tobacco is shaded from the sun with gauze. Once hung in the four-story-high drying sheds, the leaves are periodically greeted by smoke from coconut husks to aid in the curing process. Four years and dozens of additional processes later, the tobacco is hand-rolled into a cigar and stored for six months in a cedar vault before ending up in the unique, handmade boxes. Thanks to the Fuente’s deep-rooted passion to never rush the hands of time, the Fuente Fuente OpusX is released sparingly and is ranked among the world’s finest, consistently garnering scores higher than most Cubans.