Plunderers of the ports

The Spanish main was a land rich in wealth particularly gold, silver and precious gems. The pirates of the Caribbean relied on different ports in the Spanish main to plunder for treasure.  The ports were so guarded securely that it made it hard for the pirates to plunder. The reason for guarding the ports so heavy was because of the gold deposits that have been left there. For this the Pirates did not give up attacking

Some of the key port cities were Portobello and Darien in the area of present day Panama and Cartagena near present day Venezuela.

The pirates were insane for trying to invade these well guarded lands. Of course they were well aware of the method Spain used for moving treasure and they were willing to risk the dangers of the mosquito infested swamps in order to relive Spain of its wealth. The pirates would often attack at dusk, after the Spaniards had had a long and arduous march through the jungle.

The soldiers could not pursue the attackers for fear that the ambush was simply a diversion and the main attack would occur after the Spanish split up their forces. In all, the pirates had the upper hand. 

The ports themselves had shore batteries with larger cannons than the most of the pirate ships could carry. Combine with higher and thicker walls. Ports would also have Galleons on hand which would come out to greet you before you even got within cannon distance of the port.

Nevertheless, the most vulnerability in the ports was their lack of protection from the landward side. Spain assumed that the jungle was good enough protection for this area. For the most part Spain was correct. Even though the pirates and most people knew all of the ways the Spanish will guard their ports, a lot of people failed their attempts. Spain was guarded too heavily. 

However, of course Sir Henry Morgan was an exception to this rule, as was Francis Drake. His most daring accomplishment was the sacking of Portobello. What he did different was doing this action as a privateer and with the support of a large fleet commissioned by England. 

http://pirates.hegewisch.net/spmain.html

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