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. Twenty years later, he would open his own cigar factory in Havana and begin producing his own cigar line, 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 translated from Spanish to English as "the Hole of Monterrey" in reference to the concave terrain favoured 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.
In 1931, the Gener family sold their cigar brands in order to focus more on their sugarcane properties. The firm of Fernández, Palicio y Cía bought the Hoyo de Monterrey and La Escepción brands and added them to their impressive line-up, which already included Punch and Belinda. Around this time, in the 1940s, the Le Hoyo series (along with the Chateaux series which would later be used to create the Davidoff cigar line) was created for Swiss distributor A. Dürr Co. After the death of partner Ramón Fernández, Fernando Palicio became sole proprietor of the business and by 1958 his cigar lines accounted for 13% of all Havana cigar exports.
After the revolutionary government of Cuba unilaterally nationalised all the cigar manufactures in 1959, Fernando Palicio voluntarily left Cuba for Florida. He subsequently sold his cigar lines to the Villazon family, which continued to make Punch, Hoyo de Monterrey and Belinda cigars in their Tampa, Florida factory from Honduran tobacco for the American market.
Hoyo de Monterrey continued production in Cuba and in Honduras and is still a popular, globally marketed Cuban cigar line. Among connoisseurs, the Epicure No. 2, Double Coronas and Le Hoyo series are particularly prized.
Being a globally marketed brand, Hoyo de Monterrey has been chosen for Habanos' annual Edición Limitada releases since 2000. The Particular had some production problems during the first Edición Limitada line-up in 2000, with few of the cigars getting out to vendors. This prompted Habanos to release it again the next year, the only Edición Limitada cigar so far to have had this happen. In 2004, a new size was added to the Hoyo de Monterrey line, the Petit Robusto, which also wore a slightly redesigned Hoyo de Monterrey cigar band.