Pirates of the Caribbean, The pirates and their ships
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The stately ship that had been allowed to sail so leisurely into Carlisle Bay under her false colours was a Spanish privateer, coming to pay off some of the heavy debt piled up by the predaceous Brethren of the Coast, and the recent defeat by the Pride of Devon of two treasure galleons bound for Cadiz. It happened that the galleon which escaped in a more or less crippled condition was commanded by Don Diego de Espinosa y Valdez, who was brother to the Spanish Admiral Don Miguel de Espinosa, and who was also a very hasty, proud, and hot-tempered gentleman.

Galled by his defeat, and choosing to forget that his own conduct had invited it, he had sworn to teach the English a sharp lesson which they should remember. He would take a leaf out of the book of Morgan and those other robbers of the sea, and make a punitive raid upon an English settlement. Unfortunately for himself and for many others, his brother the Admiral was not at hand to restrain him when for this purpose he fitted out the Cinco Llagas at San Juan de Porto Rico. He chose for his objective the island of Barbados, whose natural strength was apt to render her defenders careless. He chose it also because thither had the Pride of Devon been tracked by his scouts, and he desired a measure of poetic justice to invest his vengeance. And he chose a moment when there were no ships of war at anchor in Carlisle Bay.

He had succeeded so well in his intentions that he had aroused no suspicion until he saluted the fort at short range with a broadside of twenty guns.

And now the four gaping watchers in the stockade on the headland beheld the great ship creep forward under the rising cloud of smoke, her mainsail unfurled to increase her steering way, and go about close-hauled to bring her larboard guns to bear upon the unready fort.

An excerpt from Captain Blood by Rafael Sabatini

Galleon

The Prize!... the Spanish Galleon

The Galleon was the ship of the line for its day. However it served the dual purpose of being both a Man-O-War and also a treasure/merchant ship. In the Golden age of Piracy, Spain has the most fortified Galleons in the water. A noticeable design of the galleon was that its hull sloped inward as it rose, tapering to a narrow top deck compared with the ship's beam at the water line. The purpose for this design was to concentrate the weight of its cannons close to the centerline of the ship in an attempt to improve stability. The galleon was heavily armed. It typically carried 74 guns, with 36 each of these being mounted on either side of the ship. The two remaining guns were mounted aft. This does not include the numerous swing guns mounted along the rail that were used to repel borders.

Despite arranging the galleons ordinance along the centerline of the ship, the ship was easily rocked by the sea. A galleon had extremely high side and an even higher stern (or Poop) deck. A galleon also had a very short keel when compared to the length of the hull. This design caused the Galleon to pitch and roll more easily than other ships. In short, if you were prone to sea sickness, you didn't want to be on a Galleon.

With that said, The Galleon was an extremely sleek ship and faster than many of her predecessors. Most galleons were four masted ships (although some were only three. The stern most mast was known as the bon-adventure mast and was rigged with a lanteen sails which gave the ship great maneuverability especially in the wind. For their size, Galleon had great speed (about eight knots).

The treasure ships as a rule, would move in convoy or flotas typically with the strongest ships hauling the most treasure. The flotas would shun contact with other ships and would invariable run rather than fight. Of course the speed of eight knots was fast for ship the size of a galleon but it was slow compared to Sloops. In the event that a Galleon couldn't outrun a foe it had several tricks up its sleeves.

The formidable firepower of its broadsides easily outmatched almost any other ship on the sea. It was foolhardy to exchange broadsides with a Spanish galleon.

If a ship actually got in close enough to attempt boarding a galleon, the galleon had razor sharp crescent blades attached to the outer most edges of its masts. The blades would rip an adversaries sails to ribbons.

Galleons had fighting platforms built half way up the mainmast and foremast. When an enemy ship attempted to board a galleon, archers from these platforms would release a shower of arrows and crossbow bolts into the attackers. (Firearms were forbidden from the fighting tops for fear of sparks from the weapons setting the sails on fire).

A typical crew would consist of around 200 to 400 men. The Galleon could also carry as many as 40 paying passengers.

Occasionally you will hear Galleons called "Galleys". This is a misnomer.

Flota and Flotilla

A Flota or Flotilla is a group of ships sailing together, typically for protection from piracy or attack from other nations. It can also be called a "fleet" or "ships sailing in convoy".

Pirate Ships

The Typical Pirate Ship

The movies usually show three masted man-o-wars for pirates ships or more lately a well armed frigate or brig. This may have been the case for the well armed privateer sailing under letter of marque but for the run of the mill caribbean pirate out on the account, an English Hoy or work sloop would be a good starting vessel.

Most sloops of the time were square rigged with a gaff sail on a single mast. The sloops were seaworthy craft used for hauling cargo over a short distance and also for fishing. (as well as smuggling and piracy). Most often the pirate began his career by stealing a small boat or sloop and working his way up to bigger and better vessels.

During the Golden Age, almost all vessels were armed to some degree. A ne'er do well pirate sloop would lash 6 to 10 cannons (depending on the size) to the top deck which would act as the gun deck. Perhaps brace of swivel guns could be mounted fore or aft. The guns were probably not as large as those on a man-o-war. On a small sloop the guns may range in sizes between 4 and 6 pounders. On rare occasion you may see the "long nines" longer barreled 9 pounders are larger sloops but normally a schooner or frigate would be required for these larger guns.

The pirates would sleep below deck (or perhaps on deck) along with their contraband. The typical crew would be twenty or eighty on a cramped sloop, depending on the number of cannons and just how big the sloop could be.

Once they would find a target they would quickly make haste back to safe waters and find a place to stash the loot. These were not the vessels to be used for long voyages and numerous strikes. These were hit and run ships.
A Pirate Flagship of the 1600s

The lucky pirate captain may have commanded a Cromster, which looks like a small galleon.

The Cromster (also spelled Crompster or Crumster) was a merchant ship by trade, relatively fast but not as maneuverable as a sloop. The Cromster has a foremast and mainmast but also supports a third mast to the rear which sporting a lanteen sail. (See the rigging for a snow by comparison) Some cromster lacked the lanteen mast at the rear and instead used a gaff sail as seen on a sloop of war or corvette.

When used as a warship, cromsters would act as escorts for the larger galleons. While the cromster lacked the speed of a sloop it would have at least twice the firepower and possible three or four times the crew. It would also hold more loot.

A cromster could have a gun deck and could also lash extra guns to its top deck. The cromster would cary between eight and sixteen guns on the gun deck ranging from 4 to 12 pounders. The crew could easily top sixty and go into the hundreds. Depending on the number of cannons the living conditions would be quite cramped.

Companies or governments, having more money than your average pirate would be more likely to outfit their privateers with ships similar to the cromster. A privateering fleet could comprise sloops, schooners, frigates and even captured galleons.

Pirates & Ships They Sailed

The following is a list of known pirates and the ships they sailed. from what I can tell, either not all pirates chose to name their ship or the name of the ship was not recorded by historians. Needless to say, some pirates sailed on more than one ship. For many pirate the favorite choice of ship was the quick and agile sloop. Note below how many ships were christened Revenge or had that word somewhere in the name.

The CaptainHis Ship
BonnetRevenge
CrowleyRevenge
Davis, HowellBuck, King James
Evans.Scowerer
GowRevenge

Bartholommew RobertsFortune, Royal Fortune, Good Fortune
GoldsmithSnapDragon
LowtherDelivery, Happy Delivery
Morgan.Oxford, The Satisfaction, and more
TeachQueen Anne's Revenge
SampleFlying King