Life of a buccaneer was usually short-lived. Usually they had a few glorious years and then destiny took its payback for all the violent crimes. Their lifestyle was full of danger and every attack on the Spanish ships and towns could end up with death. To survive all the odds, buccaneer had to be tough, skilled and lucky as well. However, when buccaneers heard about a successful and ambitious leader on the horizon, they were ready to join him without any hesitation. There were always a lot of daredevils, who waited for their chance to grab some precious piece from the Spanish treasury.
One of the key reasons, why buccaneers had success in their journeys were their great combat skills. Those buccaneers, who initially were hunters on Hispaniola, spent a lot of their spare time in challenging each other in various shooting drills. They became expert marksmen and this helped a lot in the process of capturing the Spanish ships. The fearless and violent character also played a huge role and despite the fact that Spaniards usually were superior in number, buccaneers still could beat them and seize their ships.
When they spotted a Spanish ship that looked heavy and filled with colonial goods, buccaneers tried to sneak as close as possible and board on it. Some Spanish captains gave back ships without any resistance and buccaneer captain occasionally appreciated such gesture and did not slay the crewmembers. Buccaneer ships were usually much smaller than the heavy loaded Spanish galleons. However, this gave them a great advantage – a smaller ship was easier to steer. An experienced steersman always tried to follow the same course as the pursued ship to avoid the cannonade. The best buccaneer shooters did their part and took down any gunner, who tried to get close to the cannons. When it was time to get on board, a heavily armed bunch of angry screaming and swearing men got on the Spanish deck and started to take down all the soldiers as quickly as possible. These battles usually were short and buccaneers got a great reward for their efforts.
Buccaneers were no strangers to the battles on the land as well. Their leaders occasionally brought together a large number of men and attacked the Spanish colonial towns. Some campaigns involved a retired high rank officers, who had the necessary experience and were battle tested. Tactics were similar to the ones buccaneers had in the naval battles. To attack suddenly and without any hesitation. Such approach also made sense because they did not had siege engines. Buccaneers tried to avoid positional battles and they just occasionally attacked in strict formations – only when there was no other alternative. In some cases, they used a human shield from the captured monks, nuns and other harmless civilians.
However, there is one fact to be added in fairness to the Spaniards. One of the reasons, why buccaneers were so successful in their journeys was the lack of experienced soldiers and sailors in the Spanish army and navy. Most of them were simply not good enough to cope with the buccaneers, who had plenty of experience in duels and battles. In addition, most of them basically had nothing to lose because of their flamboyant and adventurous lifestyle. Spaniards had a great disadvantage in this regard. Besides lack of experience, sailors usually had to live in miserable conditions with a poor wage, while buccaneers always had the potential to get a share from a massive loot.
Same lack of quality men in the military and navy pushed the Spanish Empire to change the situation. Ships loaded with colonial goods now got better protection and better-trained crews. When buccaneers started to cause trouble to other country ships, European authorities followed the Spanish example. Naval forces were strengthened and now sea raiders had a tougher resistance from the attacked ship crews. Colonial powers wanted to clear the Caribbean from the piracy and buccaneer influence in the region started to fade. They eventually became semi-mythical heroes of the drunk tales that were told in taverns by the old sailors around the coastal towns.
Sources | Cruz Apestegui Cardenal. Pirates in the Caribbean: Buccaneers, Privateers, Freebooters and Filibusters 1493-1720 (2002) | Colin Woodard. The Republic of Pirates: Being the True and Surprising Story of the Caribbean Pirates and the Man Who Brought Them Down (2007) | Alexandre Exquemelin. The Buccaneers of America: In the Original English Translation of 1684 | Edgars Andersons. Senie kurzemnieki Amerikā un Tobāgo kolonizācija (1970)