Havana, Cuba
Havana began to boom when commerce between Spain and her American colonies hit its stride. The town attracted numerous settlers, as yearlong breezes tempered the tropical heat and made the climate bearable for Europeans unaccustomed to the tropics.
As a seaport it had much to recommend it. Its deep-water harbor, the finest in the West Indies, could accommodate a thousand ships with ease, and the entrance to the harbor, a narrow channel, could easily be defended. By no means the least of Havana's advantages was the fact that all ships passed within sight of it on the voyage back to Spain.
Most of the ships returning to Spain not only sighted Havana, but called in there. The city provided the ships with water, with victuals from the surrounding farmland, the most fertile on Cuba, with replacements for crewmen who had died on the voyage or deserted in one of the ports the ship had visited. Above all, Havana provided timber, in which the island abounded, and became the leading shipbuilding port of the Western Hemisphere as well as a stopping-off place for ships to make repairs before beginning the long transatlantic voyage.
Not surprisingly, Havana was a port of call for all returning flotas, and was the only port in the New World consistently visited by both the Tierra Firme Flota and the New Spain Flota. The Tierra Firme Flota sailed there following the rendezvous of all the ships in Cartagena, a voyage of some ten days to two weeks. The New Spain Flota arrived from Vera Cruz; this voyage took from six to eight weeks because the ships had to sail against contrary winds and currents and had to head north, sometimes as far as the area of present-day Pensacola, before being able to come about and head south, hugging the coast of Florida as far as the Florida Keys, before sailing directly for Havana.
In the early days before the fortifications were completed, Havana had been a favorite target for enemy or pirate attack, and on many occasions it was sacked and burned to the ground. However, by 1586 when Francis Drake had intentions of attacking it, he decided against this move when he saw how strongly it was held. During the period of Spanish domination in America, of all the Spanish seaports Havana was the one least often attacked and taken by enemy fleets.
