- Battle Sails
- Be He Ever So Humble
- Be Still My Rum
- Beaksworth's Bounty
- Beans
- Beasts of England
- Beat (skill)
- Beating the Brush
- Beatrix Lyon
- Beatriz Barrosa
- Beauregard Schneider
- Beauty and the Beasts
- Beef
- Before The Wind (skill)
- Beginner's Guide
- Behind Enemy Lines
- Belize
- Belize Florentine Master
- Bella Capetillo
- Belle Isle
- Benayas's Summons
- Benedict Keene
- Benito Candelaria
- Benito Ortiz
- Benjamin Wickham
- Benoit Maisonbasse
- Bermuda Chub
- Bernadine Beaufleury
- Bernardino Cançón
- Bernardino Patudo
- Bernardo Esposito
- Bernardo Sanromá
- Bernice Mae
- Bert Harvey
- Bertrand Foucques
- Besieged Tortuga
- Best Point
- Betrayer's Ship Modification
- Better French than Dead
- Better Limey than Dead
- Better a Don than Dead
- Bey's Retreat
- Beyond the Island of the Monkeys
- Beyond the Sea
- Big Game Hunter Cannon Rigging
- Big Wreckage
- Bigger and Better
- Billy Bones
- Biloxi
- Biloxi Florentine Master
- Bit Raider
- Bitores Cotado
- Black Beach
- Black Chamber
- Black Flags or Dread Saints
- Black Heart, Black Powder
- Black Market (skill)
- Black Marketeer
- Black Point
- Black Point's Rum
- Black Powder
- Blackbeard's Gold
- Blackbeard's Journal
- Blackbeard's Legacy
- Blackbeard's Pistol
- Blackbeard's Wreck
- Blackbeard Server Victory:2007-12-31
- Blackmailer's Gloves
- Blas Retz
- Blasco Govado
- Blessing of the Sea
- Blinded by science
- Blinding Sand (skill)
- Blockade Disruption
- Blocks, Lignum Vitae
- Blocks, Oak
- Blom's Blockade
- Blood in the Water
- Bloodied
- Bloodthirst (skill)
- Bloodthirsty Scallywag
- Bloody Arms Bounty
- Bloody Kate
- Bloody Minds (skill)
- Bloody Noses
- Bloody Rampage
- Bloody Rose Society
- Bloody Tunic
- Blue Blood Stained
- Blue Harvest
- Blue Marlin
- Blue Parrot
- Bluefields
- Bluefin Tuna
- Board of Marque
- Boarding
- Boarding Axes
- Boarding Discipline (skill)
- Boarding Gear
- Boarding Grenados
- Boarding Guide
- Boarding Party Ready Positions
- Boarding Tutorial: To Arms!
- Boarding Tutorial: To Boarder's Bay!
- Boiling Point
- Bon Appétit
- Bonaire
- Bonefish
- Bonnet Server Victory 1
- Bonny Server Victory 1
- Booby Call
- Book: Basic Consumables
- Book Return
- Booty, Booty, Booty
- Booty Island Radio
- Boss's Finely-Balanced Rapier
- Boss Billings
- Bosun's Starter (skill)
- Bosun's Whip (skill)
- Botany to Go
- Boucanier's Blade
- Bound Diagrams
- Bounties and Bandits
- Bounty Missions
- Bow
- Boyle's Summons
- Brace Winches
- Brace of Pistols (skill)
- Brady Houck
- Branson Keith
- Brass Structural Bracing
- Brawler's Gloves
- Brawler's Harness
- Brawling
- Break Formation (skill)
- Break Morale (skill)
- Break the Line
- Breaking and Entering
- Breaking the Spell
- Bredan Walker
- Brendan's Bottled Grog
- Brendan Walker
- Brethren Liaison
- Brethren Quartermaster
- Brethren of the Coast
- Brian Hodgeson
- Brian Yeung
- Bribes and Misdemeanours
- Brice Damisé
- Bridgetown
- Bright Lights, Big City
- Brigitte Desgouttins
- Bring Him Back Alive
- Brisk Trade
- British East India Company
- British East India Company: Become Indifferent
- British Royal Society
- British Trade Union
- Broad Reach
- Broadsheet Peddler
- Broadside
- Brody Blackwell
- Broken Charm
- Broken Silver Compass
- Bronze Round Shot
- Bronze Seal
- Brothers in Arms
- Bruce Sharp
- Brumby's Summons
- Bruno Escalera
- Bryan Yarrow
- Bryde's Summons
- Buccaneer
- Buccaneer's Blasting Powder
- Buccaneer Trainer
- Buckskin Dueling Gloves
- Build 2.13.41.0
- Bulbous Stern Lantern
- Bulwarks
- Bulwarks, Heavy
- Bulwarks, Superior
- Bundle Unrest Supplies: Food
- Bundle Unrest Supplies: Luxuries
- Bundle Unrest Supplies: Metal
- Bundle Unrest Supplies: Textiles
- Bundle Unrest Supplies: Weapons
- Bundle Unrest Supplies: Wood
- Burden of Truth
- Burning Bridges
- Burning Sea Note
- Burning Sea Points
- Burst of Speed (skill)
- Business Trip
- Business Venture
- Business and Pleasure
- Business is Good
- Businessman's Blade
- Bust of Captain Kidd
- Bust of the King of England
- Bust of the King of France
- Bust of the King of Spain
- Buying Time
- By Popular Demand
- By the Sword
- Børge Aumaître
- Cabo Raphael
- Cacao
- Cadrick Milnes
- Caesar Grunt
- Cafra's Summons
- Caleb Smalley
- Calling on the Boss
- Calling on the Magistrate
- Campeche
- Can I Get a Witness?
- Can You Dig It?
- Caniff Highland Scotch
- Canister Shot
- Cannister Shot
- Cannon, Huge
- Cannon, Large
- Cannon, Medium
- Cannon, Small
- Cannon, Swivel Gun
- Cannon, Very Small
- Cannon ammunition
- Cannons of Heaven and Earth
- Cantonese Powder 3
- Cap'n Slappy
- Capa Ferro
- Cape de Vela
- Capital
- Capital Exchanger
- Captain's Cannon Modification
- Captain's Flintlock
- Captain's Liquor Cabinet
- Captain (title)
- Captain Billings
- Captain Billings' Bounty
- Captain Billings' Legacy
- Captain Billings' Revenge
- Captain Blood
- Captain Corpus
- Captain Heisenbergs Steering Mechanism
- Captain Heisenberg’s Steering Mechanism
- Captain Lobo
- Captain Ruenzi
- Captain Vuur
- Captain Wood's Orange Liquor
- Captain by Courtesy
- Captains Wanted
- Captive
- Captive Audience
- Captured Banner
- Captured Battle Ensign
- Captured Ensign
- Captured Pennon
- Captured Ships
- Captured Standard
- Caracas
- Carbaneras
- Cardinal Basilio
- Careening Camp
- Career
- Career: Buccaneer (skill)
- Career: Cutthroat (skill)
- Career: Freetrader (skill)
- Career: Navy (skill)
- Career: Privateer (skill)
- Career Skill Respec
- Caribbean
- Caring for Our Own
- Carlos Aledo
- Carlos Harbour
- Carlye Fuller
- Carmela el Moro
- Carmelo Fajardo
- Carmelo Heredia
- Carmen Prez
- Carole Dubray
- Carole Lafranchise
- Carole Pinet
- Carolyn Civitts
- Carrasco's Blockade
- Carribean Queen
- Cartagena
- Cartographer's Journal : Chapter I
- Cartographer's Journal : Chapter II
- Cartographer's Journal : Chapter III
- Cartographer's Journal : Chapter IV
- Cartographic Violence
- Cartography Isn't For Sissies
- Caruncho's Summons
- Carvajal
- Casimiro Tardio
- Cask of Captain's Choice Rum
- Cask of Salvation
- Cast Away
- Castañón Trinidad
- Castellano's Blockade
- Castelles' Backstabber
- Casting the Net
- Cat Island
- Cataclysm Saint
- Catala's Mast
- Catching a Break
- Catherine Royce
- Cayenne
- Cayo de Marquis
- Cebrián Mondexar
- Cecilio Galiano
- Cedric Willow
- Celebration Mask
- Celia Genevieve
- Celio Bustos
- Celio Solevila
- Certainly Not Jetsam
- Cesaire Desponts
- Cesar Bone
- Chac Kuk's Pierce
- Chain Shirt, Adequate
- Chain Shirt, Basic
- Chain Shirt, Fine
- Chain Shirt, First-Rate
- Chain Shirt, Inferior
- Chain Shirt, Outstanding
- Chain Shirt, Quality
- Chain Shirt, Shoddy
- Chain Shirt, Superior
- Chain Shirt, Well-Made
- Chain Shot
- Chain of Command
- Champagne
- Champagne Glasses
- Chantal Dubeau
- Charles Bellefleur
- Charles Farley
- Charles Johnson
- Charlesfort
- Charlestown
- Charline Demont
- Charlotte Verell
- Chasing Their Own Tails
- Chat
- Chateau Murchison Madeira
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