- Requin
- Resolve
- Restoration Doll
- Restoration Staff
- Retavick
- Retrain
- Revenant
- Revenant Cannon Ram
- Revenant Doll
- Reverse Spin Cut
- Revive
- Revive Pirates of the Caribbean Online
- Rhea Armstrong
- Rhea Armstrong Blacksmith
- Rhineworth Rings
- Ricbert Grinhook
- Rich Knee Boots
- Richard Deckman
- Richard Silveredge
- Rickets
- Rico
- Ridgeway's Revenge
- Riding Blouse
- Riding Coat
- Rigging
- Right Pincer
- Rina Redd
- Rip Tail
- Riposte
- Ripsaw Blade
- Ripshred
- Rise of the Privateer (Lore)
- River Alligators
- Roast Pork
- Rob's Guide to Material Runs
- Robber's Knives
- Robber's Musket
- Robber's Pistol
- Robber's Sea Globe
- Robert Bancair
- Robert Bristol
- Roberta Roberts
- Roberto Hierro
- Rock Crab
- Rockbottom
- Rocky
- Rococo Ricky
- Roger's Tips and Tricks to Leveling
- Roger Ironbreaker
- Rogue Privateer
- Roland Raggart
- Rolling Attack
- Roman Paine
- Romany Bev
- Romany Lara
- Romany Leander
- Rookie
- Rooster Booze
- Rose Cabinmenace
- Rose Petal Corset
- Rose Seafellow
- Rose Winsome
- Rosetta Zimm
- Rotted Shorts
- Rotted Trousers
- Rotten Scales
- Rotten Staff
- Rough Tricorne
- Rough Water Blouse
- Round Belt
- Round Buckle Belt
- Round Shot
- Roundhouse
- Roundhouse Raven
- Rowan Bowen
- Rowdy Rooster
- Rowdy Rooster Celebration (GM Event)
- Royal Anchor
- Royal Blunderbuss
- Royal Broadsword
- Royal Caverns
- Royal Chest Corset
- Royal Commodore
- Royal Cutlass
- Royal Musket
- Royal Navy
- Royal Navy Foreman's Office
- Royal Sabre
- Ruby & Onyx Double Band
- Ruby & Onyx Double Lip Ring
- Ruby & Onyx Ear Double Loop
- Ruby & Onyx Ear Rings and Stud
- Ruby & Onyx Full Nose Jewelry
- Ruby & Onyx Hoop and Rings
- Ruby & Onyx Knuckles
- Ruby & Onyx Lip Spike and Rings
- Ruby & Onyx Ring Spike
- Ruby Lip Ring
- Ruby Lip Spike
- Ruby Wynn
- Ruby and Amethyst Ear Stud and Ring
- Rudyard's Teeth
- Ruffle Shirt
- Rum
- Rum-Drunken Scorpion
- Rum Cellar
- Rumrunner's Isle
- Rumrunner's Sea Chart
- Runic Blunderbuss
- Runic Pistol
- Runic Repeater Pistol
- Runner's Capris
- Rusty Bayonet
- Rusty Cutlass
- Rusty McGinnis
- Rusty Sabre
- Rusty Throwing Knives
- Ruth Armstrong
- Rutherford Bligh
- Ruthless Julian
- Ryan's Guide to Cursed Blades
- Sabre of the Inquisition
- Sack
- Sack Shorts
- Sack Vest
- Sacred Cutlass
- Sacred Musket
- Sacred Pistol
- Sacred Repeater Pistol
- Sacred Sabre
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