picaroon
Thieving ocean wanderer
A picaroon is a rogue, vagabond, or petty thief—someone who lives by their wits on society's margins.
The word also meant a pirate or pirate ship, especially in the Caribbean during the age of sail.
It carries a flavor of adventure and roguish charm rather than serious criminality: The old picaroon had a story for every port.
Caribbean colonial-era pirate
- corsairPirate or pirate ship
- freebooterMaritime plunderer seeking booty
- privateerAuthorized civilian warship
- sea roverMaritime plunderer
raider · marauder · sea dog · cutthroat · brigand · looter · reaver · sea wolf
Dishonest, unscrupulous person
- knaveDishonest, unprincipled person
- rascalLovable troublemaker
- scalawagAffectionate term for rogue
- blackguardContemptible, dishonest person
ne'er-do-well · villain · rapscallion · scamp · ruffian · vagabond · trickster · cheat
Journey by sea
- expeditionOrganized exploratory journey
- high seasWaters beyond jurisdiction
- questSeeking journey for something
- escapadeReckless, exciting adventure
daring · perilous · swashbuckling · derring-do · seafaring · exploit · bravado · gallant
Stolen valuables
- bootyStolen valuables, especially treasure
- spoilsSeized war gains
- pillageViolent theft of goods
- raidSudden armed incursion
heist · ransack · sack · plundering · robbery · seizure · haul · prize
Large historical sailing ship
- schoonerMulti-masted sailing craft
- frigateMedium-sized naval warship
- brigantineTwo-masted mixed-rig vessel
- man-of-warArmed sailing vessel
clipper · sloop · caravel · barque · carrack · ship · vessel · mast
Element seventy-nine
- doubloonsHistorical Spanish gold currency
- pieces of eightOld Spanish coinage
- jewelsOrnamental precious stones
- chestRibcage region or strongbox
hoard · riches · coins · silver · gems · buried treasure · treasure chest · cache
buccaneer
Caribbean colonial-era pirate
- corsairPirate or pirate ship
- freebooterMaritime plunderer seeking booty
- privateerAuthorized civilian warship
sea rover · raider · marauder · sea dog · cutthroat · brigand · looter · reaver · sea wolf · plunderer
scoundrel
Dishonest, unscrupulous person
blackguard · ne'er-do-well · villain · rapscallion · scamp · ruffian · vagabond · trickster · cheat · rogue
voyage
Journey by sea
- expeditionOrganized exploratory journey
- high seasWaters beyond jurisdiction
- questSeeking journey for something
escapade · daring · perilous · swashbuckling · derring-do · seafaring · exploit · bravado · gallant · flamboyant
loot
Stolen valuables
raid · heist · ransack · sack · plundering · robbery · seizure · haul · prize · swag
galleon
Large historical sailing ship
- schoonerMulti-masted sailing craft
- frigateMedium-sized naval warship
- brigantineTwo-masted mixed-rig vessel
man-of-war · clipper · sloop · caravel · barque · carrack · ship · vessel · mast · rigging
gold
Element seventy-nine
- doubloonsHistorical Spanish gold currency
- pieces of eightOld Spanish coinage
- jewelsOrnamental precious stones
chest · hoard · riches · coins · silver · gems · buried treasure · treasure chest · cache · bullion
picaroonlawman
Enforcement officer
officer of the law · constable · sheriff · magistrate · policeman
picaroonsaint
Canonized holy person
man of honor · gentleman · paragon · philanthropist · benefactor
picaroonnaval officer
Ranked military sailor
commodore · admiral · coast guard · naval commander · customs officer