The first big smoke was called "Sik'ar" by the Taino Indians of Puerto Rico. The Taino Indians were part of the Arawak Indian culture that made their home in the Caribbean islands. They dominated the area between Cuba and Aruba.
The Taino Indians of Puerto Rico began rolling tobacco into tubes around 4,000 BC. They also invented BBQ and the Hammock. Sik'ar was a gathering of all Indians from all the islands. They would BBQ smoked meat, trade cigars and cured tobacco, tobacco seeds, their version of rum (from coconut milk) and settled land disputes, trade disagreements, charted new islands, raised armies to fight the Caribe Indians and generally had a convention and at conventions you understand people tend to have a good time. The Taino also invented the hammock. They invented the first cigars. Columbus saw tobacco rolled into tubes for the first time ever at this festival. He called the tubes of smoking tobacco "cigarros" after the festival where they were found in abundance (Sik'ar).
The Taino Indians used stone molds to make the cigars. They would roll the tobacco into bunches, tie them with strings from leaves and bark and place them between two halves of hollowed stone molds. The stone molds were wrapped tightly with string and buried until the next Sik'ar. The stone molds were retrieved, the strings were cut and the bundled cigar was wrapped in any dry vegetable leaf (most of the time another tobacco variety) and smoked.
Needless to say thousands of cigars changed hands and were smoked. Imagine that !