Cigars have a relatively modern history, compared with the long history of tobacco, and it coincides with Columbus' discovery of the new world. When Columbus sailed west in 1492 searching for a spice route, he encountered native cultures around the Carribean that cultivated tobacco, including Cuba where Columbus settled for a period of time. The natives smoked a primitive ancestor of the cigar which was often wrapped in non-Tobacco leaves, such as palm or plantain. Several of the Columbus' explorers then brought this tradition back with them to Europe. The sailors and conquistadors introduced the habit to the citizens of Spain and the rest of Europe, where the practice was a sign of wealth. Initially cigar smoking was considered a pagan ritual (from the ritualistic smoking among native populations in the Americas) and smokers were imprisoned, although the practice soon became accepted.
As popularity grew, tobacco seed was transplanted to other growing regions worldwide, including the far east and the newly founded American states in the 1600's. Most colonists however, were smoking pipes rather than cigars. The modern variant of the cigar is generally considered to have been started in Spain during the early 18th century. As cigar production slowly spread through Western Europe (called a segar in Europe), cigar smoking became seen as very fashionable. It didn't really take off in France and Britain until after the Napoleonic wars when soldiers returning from service in Spain brought the habit with them.
In Seville, Spain, where most of the Spanish and even European cigar production took place in the 1700's and 1800's, the raw materials for cigar production were imported from Cuba. It wasn't until 1821 that Cuba was permitted to produce cigars for export to Europe, and in appreciation, the Cubans would send a box of their finest cigars (Trinidads) to the Spanish king every year. Today, Cuban cigars are still considered among the worlds finest, although trade embargoes have allowed other countries to rise to the same level of quality.
Cigar smoking in America didn't start until a little later, in the mid to late 1700's when an American Revolutionary War general returned from service in Cuba to his home in Connecticut with cigars and tobacco. A burgeoning cigar industry started up in the Hartford area and tobacco growing soon followed. Today, many of the finest cigars use Connecticut shade leaf tobacco for wrappers. By the 19th century both Cuban cigars and domestic cigar production began to take off. Cigar smoking was far more common in the 19th and early 20th century than cigarettes. Today, as a remnant of cigar smokings' association with wealth and prosperity, many special occassions are celebrated with a fine cigar.