The indigenous inhabitants of the islands of the Caribbean Sea, Mexico, and Mesoamerica have smoked cigars since as early as the 10th century, as evidenced by the discovery of a ceramic vessel at a Mayan archaeological site in Uaxactún, Guatemala. The vessel was decorated with the painted figure of a man smoking a primitive cigar.

Explorer Christopher Columbus is generally credited with the introduction of tobacco to Europe. Two of Columbus's crewmen during his 1492 journey, Rodrigo de Jerez and Luis de Torres, are said to have encountered tobacco for the first time on the island of San Salvador in the Bahamas, when natives presented them with dry leaves that spread a peculiar fragrance. Tobacco was widely diffused among all of the islands of the Caribbean and therefore they again encountered it in Cuba, where Columbus and his men had settled.

Around 1592, the Spanish galleon San Clemente brought 50 kilograms (110 lb) of tobacco seed to the Philippines over the Acapulco-Manila trade route. The seed was then distributed among the Roman Catholic missions, where the clerics found excellent climates and soils for growing high-quality tobacco on Philippine soil.

In the 19th century, cigar smoking was common, while cigarettes were still comparatively rare. The cigar business was an important industry, and factories employed many people before mechanized manufacturing of cigars became practical. Many modern cigars, as a matter of prestige and quality, are still rolled by hand, most especially in Central America and Cuba: some boxes bear the phrase totalmente a mano (totally by hand) or hecho a mano (made by hand).