When the buccaneers elected their first captain, they had made but few determined forays against the Spaniards. The greater number of them were French cattle hunters dealing in boucanned meat, hides, and tallow. A few hunted wild boars; a few more planted tobacco of great excellence, with a little sugar, a little indigo, and a little manioc. Among the company were a number of wild Englishmen, of the stamp of Oxenham, who made Tortuga their base and pleasure-house, using it as a port from which to sally out to plunder Spanish ships. After a cruise, these pirates sometimes went ashore for a month or two of cattle hunting. Often enough, the French cattle hunters took their places on the ships. The sailors and huntsmen soon became amphibious, varying the life of the woods with that of a sailor, and sometimes relaxing after a cruise with a year's work in the tobacco fields. In 1638, when the Spanish made their raid, there were considerable numbers (certainly several hundreds) of men engaged in these three occupations. After the raid they increased in number rapidly; for after the raid they began to revenge themselves by systematic raids upon the Spaniards—a business which attracted hundreds of young men from France and England. After the raid, too, the French and English Governments began to treat the planters of the St Kitts colony unjustly, so that many poor men were forced to leave their plots of ground there. These men left the colonies to join the buccaneers at Tortuga, who soon became so numerous that they might have made an independent state had they but agreed among themselves. This they could not do, for the French had designs upon Tortuga. A French garrison was landed on the island, seemingly to protect the French planters from the English, but in reality to seize the place for the French crown. Another garrison encamped upon the coast of the larger island. The English were now in a position like that of the spar in the tale.[8] They could no longer follow the business of cattle hunting; they could no longer find an anchorage and a ready market at Tortuga. They were forced, therefore, to find some other rendezvous, where they could refit after a cruise upon the Main. They withdrew themselves more and more from the French buccaneers, though the two parties frequently combined in enterprises of danger and importance. They seem to have relinquished Tortuga without fighting. They were less attached to the place than the French. Their holdings were fewer, and they had but a minor share in the cattle hunting. But for many years to come they regarded the French buccaneers with suspicion, as doubtful allies. When they sailed away from Tortuga they sought out other haunts on islands partly settled by the English.

In 1655, when an English fleet under Penn and Venables came to the Indies to attack the Spaniards, a body of English buccaneers who had settled at Barbadoes came in their ships to join the colours. In all, 5000 of them mustered, but the service they performed was of poor quality. The combined force attacked St Domingo, and suffered a severe repulse. They then sailed for Jamaica, which they took without much difficulty. The buccaneers found Jamaica a place peculiarly suited to them: it swarmed with wild cattle; it had a good harbour; it lay conveniently for raids upon the Main. They began to settle there, at Port Royal, with the troops left there by Cromwell's orders. They planted tobacco and sugar, followed the boucan, and lived as they had lived in the past at Hispaniola. Whenever England was at war with Spain the Governor of the island gave them commissions to go privateering against the Spanish. A percentage of the spoil was always paid to the Governor, while the constant raiding on the Main prevented the Spaniards from attacking the new colony in force. The buccaneers were thus of great use to the Colonial Government. They brought in money to the Treasury and kept the Spanish troops engaged. The governors of the French islands acted in precisely the same way. They gave the French buccaneers every encouragement. When France was at peace with Spain they sent to Portugal ("which country was then at war with Spain") for Portuguese commissions, with which the buccaneer captains could go cruising. The English buccaneers often visited the French islands in order to obtain similar commissions. When England was at war with Spain the French came to Port Royal for commissions from the English Governor. It was not a very moral state of affairs; but the Colonial governors argued that the buccaneers were useful, that they brought in money, and that they could be disowned at any time should Spain make peace with all the interloping countries.

The buccaneers now began "to make themselves redoubtable to the Spaniards, and to spread riches and abundance in our Colonies." They raided Nueva Segovia, took a number of Spanish ships, and sacked Maracaibo and western Gibraltar. Their captains on these raids were Frenchmen and Portuguese. The spoils they took were enormous, for they tortured every prisoner they captured until he revealed to them where he had hidden his gold. They treated the Spaniards with every conceivable barbarity, nor were the Spaniards more merciful when the chance offered.

The buccaneers, French and English, had a number of peculiar customs or laws by which their strange society was held together. They seem to have had some definite religious beliefs, for we read of a French captain who shot a buccaneer "in the church" for irreverence at Mass. No buccaneer was allowed to hunt or to cure meat upon a Sunday. No crew put to sea upon a cruise without first going to church to ask a blessing on their enterprise. No crew got drunk, on the return to port after a successful trip, until thanks had been declared for the dew of heaven they had gathered. After a cruise, the men were expected to fling all their loot into a pile, from which the chiefs made their selection and division. Each buccaneer was called upon to hold up his right hand, and to swear that he had not concealed any portion of the spoil. If, after making oath, a man were found to have secreted anything, he was bundled overboard, or marooned when the ship next made the land. Each buccaneer had a mate or comrade, with whom he shared all things, and to whom his property devolved in the event of death.[9] In many cases the partnership lasted during life. A love for his partner was usually the only tender sentiment a buccaneer allowed himself.

When a number of buccaneers grew tired of plucking weeds[10] from the tobacco ground, and felt the allurement of the sea, and longed to go a-cruising, they used to send an Indian, or a negro slave, to their fellows up the coast, inviting them to come to drink a dram with them. A day was named for the rendezvous, and a store was cleared, or a tobacco drying-house prepared, or perhaps a tent of sails was pitched, for the place of meeting. Early on the morning fixed for the council, a barrel of brandy was rolled up for the refreshment of the guests, while the black slaves put some sweet potatoes in a net to boil for the gentlemen's breakfasts. Presently a canoa or periagua would come round the headland from the sea, under a single sail—the topgallant-sail of some sunk Spanish ship. In her would be some ten or a dozen men, of all countries, anxious for a cruise upon the Main. Some would be Englishmen from the tobacco fields on Sixteen-Mile Walk. One or two of them were broken Royalists, of gentle birth, with a memory in their hearts of English country houses. Others were Irishmen from Montserrat, the wretched Kernes deported after the storm of Tredah. Some were French hunters from the Hispaniola woods, with the tan upon their cheeks, and a habit of silence due to many lonely marches on the trail. The new-comers brought their arms with them: muskets with long single barrels, heavy pistols, machetes, or sword-like knives, and a cask or two of powder and ball. During the morning other parties drifted in. Hunters, and planters, and old, grizzled seamen came swaggering down the trackways to the place of meeting. Most of them were dressed in the dirty shirts and blood-stained drawers of the profession, but some there were who wore a scarlet cloak or a purple serape which had been stitched for a Spaniard on the Main. Among the party were generally some Indians from Campeachy—tall fellows of a blackish copper colour, with javelins in their hands for the spearing of fish. All of this company would gather in the council chamber, where a rich planter sat at a table with some paper scrolls in front of him.

As soon as sufficient men had come to muster, the planter[11] would begin proceedings by offering a certain sum of money towards the equipment of a roving squadron. The assembled buccaneers then asked him to what port he purposed cruising. He would suggest one or two, giving his reasons, perhaps bringing in an Indian with news of a gold mine on the Main, or of a treasure-house that might be sacked, or of a plate ship about to sail eastward. Among these suggestions one at least was certain to be plausible. Another buccaneer would then offer to lend a good canoa, with, perhaps, a cask or two of meat as sea-provision. Others would offer powder and ball, money to purchase brandy for the voyage, or roll tobacco for the solace of the men. Those who could offer nothing, but were eager to contribute and to bear a hand, would pledge themselves to pay a share of the expenses out of the profits of the cruise. When the president had written down the list of contributions he called upon the company to elect a captain. This was seldom a difficult matter, for some experienced sailor—a good fellow, brave as a lion, and fortunate in love and war—was sure to be among them. Having chosen the captain, the company elected sailing masters, gunners, chirurgeons (if they had them), and the other officers necessary to the economy of ships of war. They then discussed the "lays" or shares to be allotted to each man out of the general booty.

Those who lent the ships and bore the cost of the provisioning, were generally allotted one-third of all the plunder taken. The captain received three shares, sometimes six or seven shares, according to his fortune. The minor officers received two shares apiece. The men or common adventurers received each one share. No plunder was allotted until an allowance had been made for those who were wounded on the cruise. Compensation varied from time to time, but the scale most generally used was as follows[12]:—"For the loss of a right arm six hundred pieces of eight, or six slaves; for the loss of a left arm five hundred pieces of eight, or five slaves; for a right leg five hundred pieces of eight, or five slaves; for a left leg four hundred pieces of eight, or four slaves; for an eye one hundred pieces of eight, or one slave; for a finger of the hand the same reward as for the eye."

In addition to this compensation, a wounded man received a crown a day (say three shillings) for two months after the division of the spoil. If the booty were too little to allow of the declaration of a dividend, the wounded were put ashore at the port of rendezvous, and the adventurers kept the seas until they had enough to bring them home.

In the years of buccaneer prosperity, when Port Royal was full of ruffians eager to go cruising, the proceedings may often have been less regular. A voyage was sometimes arranged in the taverns, where the gangs drank punch, or rumbo, a draught of rum and water (taken half-and-half, and sweetened with crude sugar) so long as their money lasted. If a gang had a ship, or the offer of a ship, and had but little silver left them from their last cruise, they would go aboard with their muskets, shot, and powder casks, trusting to fortune to obtain stores. Nearly every ship's company had a Mosquito Indian, or more than one, to act as guide ashore, in places where a native's woodcraft was essential to a white man's safety. At sea these Indians supplied the mariners with fish, for they were singularly skilful with the fish spear. When a gang of buccaneers put to sea without provisions, they generally steered to the feeding grounds of the sea-turtles, or to some place where the sea-cows, or manatees, were found.[13] Here the Indians were sent out in small canoas, with their spears and tortoise irons. The spears were not unlike our modern harpoons. The tortoise irons were short, heavy arrow heads, which penetrated the turtle's shell when rightly thrown. The heads were attached to a stick, and to a cord which they made of a fibrous bark. When the blow had gone home, the stick came adrift, leaving the iron in the wound, with the cord still fast to it. When the turtles had been hauled aboard, their flesh was salted with the brine taken from the natural salt-pans to be found among the islands. When a manatee was killed, the hide was stripped away, and hung to dry. It was then cut into thongs, and put to various uses. The buccaneers made grummets, or rings, of it, for use in their row boats instead of tholes or rowlocks. The meat of manatee, though extremely delicate, did not take salt so readily as that of turtles. Turtle was the stand-by of the hungry buccaneer when far from the Main or the Jamaican barbecues. In addition to the turtle they had a dish of fish whenever the Indians were so fortunate as to find a shoal, or when the private fishing lines, of which each sailor carried several, were successful. Two Mosquito Indians, it was said, could keep 100 men in fish with no other weapons than their spears and irons. In coasting along the Main, a buccaneer captain could always obtain sufficient food for his immediate need, for hardly any part of the coast was destitute of land-crabs, oysters, fruit, deer, peccary, or warree. But for a continued cruise with a large crew this hand-to-mouth supply was insufficient.

The buccaneers sometimes began a cruise by sailing to an estancia in Hispaniola, or on the Main, where they might supply their harness casks with flesh. They used to attack these estancias, or "hog-yards," at night. They began by capturing the swine or cattle-herds, and threatening them with death should they refuse to give them the meat they needed. Having chosen as many beeves or swine as seemed sufficient for their purpose, they kicked the herds for their pains, and put the meat in pickle.[14] They then visited some other Spanish house for a supply of rum or brandy, or a few hat-loads of sugar in the crude. Tobacco they stole from the drying-rooms of planters they disliked. Lemons, limes, and other anti-scorbutics they plucked from the trees, when fortune sent them to the coast. Flour they generally captured from the Spanish. They seldom were without a supply, for it is often mentioned as a marching ration—"a doughboy, or dumpling," boiled with fat, in a sort of heavy cake, a very portable and filling kind of victual. At sea their staple food was flesh—either boucanned meat or salted turtle. Their allowance, "twice a day to every one," was "as much as he can eat, without either weight or measure." Water and strong liquors were allowed (while they lasted) in the same liberal spirit. This reckless generosity was recklessly abused. Meat and drink, so easily provided, were always improvidently spent. Probably few buccaneer ships returned from a cruise with the hands on full allowance. The rule was "drunk and full, or dry and empty, to hell with bloody misers"—the proverb of the American merchant sailor of to-day. They knew no mean in anything. That which came easily might go lightly: there was more where that came from.