r/ImaginaryPirates • • Jan 31 '21

Cartographer Kyla Morgan - by Bob Kehl

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2.1k Upvotes

r/ImaginaryPirates • • Oct 30 '25

Sarah Fortune by @SleinYesWowNC

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1.7k Upvotes

r/ImaginaryPirates • • Oct 10 '25

Edward Kenway by Karl Kopinski

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1.3k Upvotes

r/ImaginaryPirates • • Oct 25 '25

Herja by Maithe Carvalho

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1.1k Upvotes

r/ImaginaryPirates • • Jun 01 '21

Original Content Welcome to the free world - by Bob Kehl

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1.1k Upvotes

r/ImaginaryPirates • • Oct 08 '25

Lost Island by Andrey Vasilchenko

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1.0k Upvotes

r/ImaginaryPirates • • Jan 07 '21

Barbarian Chic, by Filipe Pagliuso

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1.0k Upvotes

r/ImaginaryPirates • • Jun 04 '26

"The terror of the seas" by Anton Prusov (Myrtille)

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970 Upvotes

r/ImaginaryPirates • • Mar 08 '26

Commission by ArtofSunnie

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945 Upvotes

r/ImaginaryPirates • • Mar 20 '26

Pirate Captain by Caio Santos

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894 Upvotes

r/ImaginaryPirates • • Mar 24 '26

slaanesh worshipping void pirate by 101ho

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868 Upvotes

r/ImaginaryPirates • • Feb 14 '21

Pirate Ship by Nikolay Razuev

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836 Upvotes

r/ImaginaryPirates • • Oct 11 '25

Original Content Moonlit pirate ship in a storm (oil painting by me)

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821 Upvotes

r/ImaginaryPirates • • May 03 '21

Original Content Pirate Harpooner - by Bob Kehl

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814 Upvotes

r/ImaginaryPirates • • Jul 19 '26

Original Content Why Can't You Just Stab Them Like Everyone Else? by me, 2026 NSFW

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786 Upvotes

r/ImaginaryPirates • • Jan 22 '21

Pirate Fire Dancer by Bob Kehl

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753 Upvotes

r/ImaginaryPirates • • Oct 19 '21

Chameleon pirate by Rinotuna

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719 Upvotes

r/ImaginaryPirates • • Sep 28 '21

Space Pirates by thdark

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688 Upvotes

r/ImaginaryPirates • • Sep 06 '21

The Demon Pirate LeChuck by Bram Sels

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679 Upvotes

r/ImaginaryPirates • • Oct 18 '20

Original Content Ye Ol Turt Tavern - by Bob Kehl

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654 Upvotes

r/ImaginaryPirates • • Nov 09 '25

Astral Shark Pirate by @SqueakyArt

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639 Upvotes

r/ImaginaryPirates • • Jul 01 '21

Original Content Rum Runners of the Ocean Blue! - by Bob Kehl

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629 Upvotes

r/ImaginaryPirates • • Sep 01 '21

Pirate Girl by Aylar Ghasemi

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610 Upvotes

r/ImaginaryPirates • • Apr 04 '21

Boarding Barbary Pirates by Andrei D

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590 Upvotes