- Revive (skill)
- Ricardo Amador
- Richard de Crevette
- Rick Saada
- Riddering's Beach
- Riddle Me This
- Ride the Wind (skill)
- Riders of the Cursed Rose
- Riding High
- Riding Rocks
- Rigging
- Rihana
- Rio de la Hacha
- Riposte (skill)
- Rival Company
- River
- Road Scholar
- Roar (skill)
- Roaring Vassal
- Robert Deal
- Roberto Asante
- Roch Descault
- Roch Sevestre
- Roch du Pont
- Rodolph Aimé
- Rodrigo Soledad
- Rodrigue's Pistol
- Rodrigue Audouin
- Rogue's Cannon Modification
- Roland Sulte
- Rolando Cotado
- Romain Carlos
- Romeo
- Ronald Rutger
- Rooting Out the Rats
- Rosalinda Diaz
- Rosalinda Pelayo
- Roseau
- Rosemary Buckley
- Rosette Sire
- Rosignol
- Rosignol Dirty Fighting Master
- Rosignol Fencing Master
- Rosignol Florentine Master
- Ross Dawking
- Rotten to the Core
- Round Shots
- Roving No More
- Rowe's Pistol
- Roy's Special Mix
- Royal Commendation
- Royal Encomium
- Royal Hull Modification
- Royal Navy
- Royal Shipyard Plans
- Ruby Pendant
- Ruddy Cove
- Rudolph Deneau
- Ruenzi's Pistol
- Rum
- Rum Punch
- Rum Ration (skill)
- Rum Runner's Sails
- Run Out the Guns!
- Run Them Down (skill)
- Run Through (skill)
- Running Dark (skill)
- Running Late
- Running With The Wind
- Ruse (skill)
- Russell Williams
- Rusty Saw
- Ryan Samul
- Saada's Banana Liquor
- Sabanqui
- Saboteur's Cutlass
- Saboteur's Rapier
- Saboteur's Small Sword
- Sack of Beans
- Sacrifice For Damage (skill)
- Sacrifice For Speed (skill)
- Sacrifice For Victory (skill)
- Safety First
- Sail Outfitting, Colossal
- Sailcloth
- Sailhandling Drills (skill)
- Sailing Guide
- Sails
- Saint Nicolas
- Salmagundi
- Salomon Deschamps
- Salomon Nez
- Salomon Zabala
- Salon d'Aventure
- Salt Mined
- Saltpeter
- Saltpeter Caves
- Salvador Callar
- Salvaged Cannons
- Salvaged Gun Carriages
- Samantha Velazquez
- Samingeom
- Samson Honeybone
- Samuel Bunn
- Samuel Howard
- Samuel Huxley
- San Juan
- San Marcos
- Sanctioned Piracy (skill)
- Sandbox
- Sandra William
- Sanson Marroqui
- Santa Catalina
- Santa Clara
- Santa Theresa's Sacramental Wine
- Santiago
- Santiago Ahoy!
- Santiago Cafra
- Santo Domingo
- Sapphire Pendant
- Sara Langewech
- Sara Tarrega
- Sarah Cox
- Saucy Jack
- Savage Cliffs
- Save Our Shipment
- Saved by the Diving Bell
- Scapegoats
- Scatter Shot (skill)
- Scatter the Competition
- Scavenge (skill)
- Scavenger's Hold
- Scholarly Pursuit
- Scientific Pursuits
- Scorched Earth
- Scoundrel's Loop (skill)
- Scourge of the Seven Seas
- Scout Hull, Medium
- Scout Hull, Small
- Scouting for Gold
- Scrapper (skill)
- Scraps of a Cannon Schematic, 1
- Scraps of a Cannon Schematic, 2
- Scraps of a Chemistry Manual, 1
- Scraps of a Chemistry Manual, 3
- Screened Kick (skill)
- Scuttle
- Scuttlebutt to Cartagena
- Scuttlebutt to Gibara
- Scuttlebutt to Iguana
- Scuttlebutt to La Isabela
- Scuttlebutt to Pointe-à-Pitre
- Scuttlebutt to Port-of-Spain
- Scuttlebutt to Port Royal
- Scuttlebutt to Puerto del Principe
- Scuttlebutt to Roseau
- Scuttlebutt to San Juan
- Scuttlebutt to Spanish Town
- Sea Dogs
- Sea Legs
- Sea Madness
- Sea combat
- Seabass
- Sean Selitrennikoff
- Second Rate Hull
- Second Rate Keel
- Second Wind (skill)
- Secret Cove Shipyard
- Secret Recipes
- Secrets Revealed
- Secrets and Spies
- Secrets of Manufacturing
- Secrets of Production
- Secrets of Shipbuilding
- Seed-Reselling
- Seeds of Destruction
- Seeing Green
- Seeing the Sights
- Segert Skips Town
- Seize Initiative (skill)
- Selitrennikoff Private Reserve
- Selling Out
- Send in the Hounds
- Serafina Fandino
- Serafina el Tigre
- Seraphine Fourquin
- Serena's Sword
- Serena Aguirre
- Sergeant Major Billings
- Serious Setbacks
- Serpent's Venom
- Server:Antigua
- Server:Bellamy
- Server:Bellamy/Victory
- Server:Bonnet
- Server:Bonnet/Victory
- Server:Bonny
- Server:Bonny/Victory
- Server:Defiant/Victory
- Server:Guadeloupe
- Server:Guadeloupe/Victory
- Server:Hornigold
- Server:Hornigold/Victory
- Server:Invincible
- Server:Invincible/Victory
- Server:Kidd
- Server:Kidd/Victory
- Server:Morgan
- Server:Morgan/Victory
- Server:Roberts
- Server:Test Server
- Server:Test Server/Victory
- Server:antigua/Victory
- Server:blackbeard
- Server:blackbeard/Victory
- Server:caribbean
- Server:caribbean/Victory
- Server:defiant
- Server:defiant/Victory
- Server:invincible/Victory
- Server:rackham
- Server:rackham/Victory
- Server:roberts/Victory
- Servicing the Escorts
- Seth "the Pit Boss" Roy
- Setting the Stage
- Settling Accounts
- Seven Deadly Sins
- Seymour Metcalf
- Shackled Shipmates
- Shame and Blame
- Shard of the Idol
- Shark-Infested Waters
- Shark-Tooth Bracelet
- Shark Hunt
- Sharktooth Clash
- Sharktooth Raiders Bounty
- Sharp's Blackout Stout
- Sharp-Eyed Lookout
- Shatter Armor (skill)
- Sheila's Poultice
- Sheila Barylett
- Sherlocke Rowe
- Shield of Faith
- Shin Kick (skill)
- Ship
- Ship's Cat
- Ship Capture, Build 26 & Other Changes
- Ship Companion
- Ship Deed
- Ship Fittings, Brass
- Ship Fittings, Iron
- Ship Jumping
- Ship Overview by Capacity
- Ship Overview by Level
- Ship Overview by Speed
- Ship Provisioning
- Ship Stem
- Ship Types
- Ship of the Line
- Ship stats tool
- Ships of the Damned?
- Shipwright's Overhaul, Average
- Shipwright's Overhaul, Crude
- Shipyard
- Shipyard, Large
- Shipyard, Medium
- Shipyard, Small
- Shoorai's Trickery
- Shoorai Edeline
- Shop
- Shove (skill)
- Shovel Ready
- Show Off (skill)
- Show of Force (skill)
- Showdown
- Shred Armor (skill)
- Shred Sails (skill)
- Shrunken Heads
- Shumate's First Mate's Rum
- Siccus Telum
- Sick in the Headland
- Sightless Corseca
- Sightless Watchman
- Sign of the Times
- Signals (skill)
- Signature of a Brewer's Manual, 1
- Signature of a Brewer's Manual, 2
- Signed in Blood
- Signet Ring of the Crime Lord
- Sigurd Langstraat
- Silence is Golden
- Silver-Plated Pistol
- Silver-inlaid Pistol
- Silver Blade
- Silver Cross
- Silver Deposits
- Silver Earrings
- Silver Goblet
- Silver Madonna
- Silver Necklace
- Silver Pendant
- Silver Plaque
- Silver Ring
- Silver Seal
- Silver Skull
- Silvestre Salvador
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