Schooner
Brig
Frigate
Man-of-War
A small, typically two-masted Vessel quite popular amongst Pirates for their Speed and Agility. Schooners are much more quick and agile when compared to other larger Vessels like Frigates and Galleons, are capable of traversing shallow Waters and Shorelines, and can carry enough Cannons to not only intimidate Merchant Vessels but also hold their own in Fights against larger Ships. On the other Hand, Schooners have less room for Cargo and Crew, resulting in small Hauls and small Crews. The Pirate Benjamin Hornigold captained a Schooner called the Benjamin during his Career.
A Brig is a two-masted Vessel that is roughly the same Size as a Frigate, though slightly smaller and with fewer Decks. Since it is larger than a Schooner, a Brig is somewhat slower and less agile, though many Pirates find this a fair Trade-off, for a larger Ship means more Cannons, Crew, and Cargo that can be carried. Despite having a reasonable Blend of these Factors, Brigs captained by Pirates was quite rare in the Caribbean during the Golden Age. The Pirate Charles Vane commanded a Brig named the Ranger during his Career.
A three-masted Ship that made up the Core of any naval Fleet during the Age of Sail, and made any Pirate a Force to be reckoned with. Frigates under the command of a Pirate were quite uncommon, but those that were intimidated many a Merchant and sunk Dozens of military Vessels. Frigates sport multiple Decks below the main Deck, some even sporting Aftcastles (such as the One depicted here) or Forecastles, and numerous Guns; some can have over forty Cannons on both Sides as well as Chase Guns. The infamous Pirate Edward "Blackbeard" Thatch captained a Frigate called the Queen Anne's Revenge until his Death.
The largest Ships available, Man-of-Wars, or simply Man O' Wars, were the most deadly and dangerous to ever sail the Caribbean. Even though they have three large Masts, Man O' Wars are quite slow, having more Decks than a Frigate (three Gun Decks) and carrying even more Cannons (~124 total: four at the Bow, eight at the Stern, and 56 on each Broadside). In the Royal Navy, Man O' Wars were commonly used as Ships of the Line, an old naval Tactic where numerous large Ships, like Men O' War, formed a Line with their Broadsides facing the Enemy, decimating them in a hail of Cannofire. Men O' War under the Command of a Pirate was rare, but not unheard of. The Pirate Bartholomew Roberts commanded a Man O' War called the Royal Fortune during his career.
A Captain is Only as Good as His Ship
If you were a Thief, where do you think the best place to gather your Riches would be? A Bank? A wealthy CEO's Home? A Drug Lord's Panic Room? These might be the Case for Today, but during the Golden Age, Riches were fastened in the Cargo Holds of Merchant Ships sailing the Seven Seas. A single Pirate can't steal vast Amounts of Cargo all by his lonesome, now can he? Nope, which is why every successful Pirate had his own powerful and sleek Vessel to captain. Numerous Types of seafaring Vessels were designed and made throughout the Age of Sail, and Pirates used any and All Classes to get the Job done. Here are but a Few of the Vessels a Pirate during the Golden Age might have used to gather his Fortune and destroy any Enemies that were stupid enough to get in their Way.