In 1831, Don José Gener y Batet emigrated to Cuba from Spain at the age of thirteen, where he worked on his uncle's plantation in Vuelta Abajo. Gener foresaw the ample potential of this trade, and in 1851 he convinced his uncle to open a factory in Havana. He created a new trademark for this industry, La Escepción, which used to try to get into the American market.  Gener was a tobacconist who personally controlled both harvesting and tobacco manufacturing process. His hands on experience is credited for both the successful marketing and pure qaulity his habanos. He invested the profits in purchasing the best farms and plantations in Vuelta Abajo, Pinar del Río, mainly the areas close to San Juan y Martinez. Gener acquired the Hoyo de Monterrey plantation in 1860, with which he tried to capitalize the success of La Escepción. 

In 1865, after using his factory's profits to acquire one of the best tobacco farms in Vuelta Abajo, he registered a cigar line named for it: Hoyo de Monterrey. Literally translating from Spanish to English as "the hole of Monterrey" in reference to the concave terrain favored by growers of premium tobacco, the brand became incredibly popular, especially in the British market, and José Gener's factory subsequently became one of the largest factories in Cuba. 

In 1900, Gener died in Spain and his daughter Lutgarda Gener took over the business and it would stay in the family for another thirty years.

The modern day Hoyo de Monterrey label represents two brands of premium cigar, one produced on the island of Cuba for Habanos SA, the Cuban state-owned tobacco company, and the other produced in Honduras for General Cigar