"The Widow's Blush - A pirate caravel, with black hull and black sails. The ship is enchanted such that any non-black paint sloughs off, and sails slowly turn black within a day of being hung. The ship's crew is grim and brooding, partly due to their dark atmosphere."

Random Generators for everything pirates, swashbuckling and seafaring.

Fantasy Gen Guides - Pirates and Seas | Dark Fantasy | Dungeons | Dungeon Maps | Pets | Pathfinder 1e | Warhammer Fantasy Roleplay

Disclaimer: I'm an affiliate for DriveThru RPG and DM's Guild

Ships

Whether you're pillaging, pirate hunting or exploring the seas, ships will be involved.

Starting with just ship names Seventh Sanctum has Pirates and Non-Pirate ships. For names and brief descriptions try Donjon's fantasy Ship generator. DND Speak's Ship Names and Description gives a short description of a pirate ship.

For details about the crew try the Pirate Crew Generator from Enead Games. And for more naming options there's a Crew Name generator

I have yet to find a generator for ship layouts but there are DriveThruRPG pdfs of a pirate ship and sailing ship

Pirates and other Sailors

For fearsome pirate names Fantasy Name Generators produced Darby "Nightmare" Law and Cassie "Yellow Teeth" Seymour while springhole.net introduced "Cutlass Breath Jenny" and "Blade Wilmot". Ennead Games has a Pirate Ship & Crew Generators which gives names and their positions on ship

For a full description springhole's Pirate Character generator gives

"This pirate is female with green eyes, a fair complexion, and wavy brown hair in a mid-length braid. She wears a pair of mid-length trousers, a corset, and goes barefoot. She also wears a silver ring and a mid-length vest. She is missing an arm, is a little touched in the head, and is an excellent navigator."

Or DnD Speak's 100 Interesting Pirates provides

"Captain Syrian Blackhand, human captain of The Ocelot - Made a pact with the god of the seas. His ship is the fastest in the world, but every year he must return to the temple where the accord was struck and cut off one finger. His left hand has only the thumb left."

To round out marine characters add a tattoo such as a "faded tiger on the upper thigh from a tribal initiation". Or a charm like "A small gold charm with a hearth and two serpents on the front and the same on the back".

The Open Sea

For creatures of the waves Fantasy Name Generators helps you name them with Sea Creatures such as "Chigrax" or "The Horned World Fish" and mermaids/mermen like "Nireta" or "Marsious". Or perhaps a giant sea turtle, "Romnal the Zaratan". Perhaps you'll meet something from the Aquatic Species Generator by Unorthodox Creativity.

For your journey this weather forecast generator predicts

"Today there will be lightning with a slight chance of drizzling rain and very slight winds from the southeast. Local guides' predictions are usually unreliable."

You might want a sea travel event such as "The carcass of a dragon turtle, bloated with decomposition gases, floats on the surface. The sickening stench is notable a half-mile away." or something for the beach like "A shrine to a maritime deity, shells and ribbons laid at its idol’s feet. A tired, old, snappy priestess and her bored apprentice live in a shack nearby and maintain the shrine."

Lastly there's a pdf of seafaring encounters at DriveThruRPG or I've produced a Sea Adventures pdf of random tables for D&D 5E at the DM's Guild.

The Places You'll See

For an island to explore try the Polygon Map Generator or play around with Azgaar's Fantasy Map Generator. If you are after island map tiles I found a pdf, Tropical Islands - Map Tile Set.

To add detail to your island add some shipwreck descriptions or at try 100 Uncharted Islands. I got

"The palace of a cloud giant that fell from the clouds and into the sea. Untold riches line the halls, but nobody's ever returned to cash in on their fortune."

For something nearer civilisation try pirate coves such as "Skeleton Lagoon" or "Port of Booty". They might contain a treasure trove. My pirates buried

One large vase, one huge glass, one suit of gold plate mail, three gold coins, sixteen pairs of dark bronze boots and seven bird skulls.

Perhaps you'll visit the harbours of "Hasshaw Landing" or "New Meadow Wharf", visiting an inn such as "The Cursed Axe" and speaking to some of the patrons.

Final Trinkets

To finish of the journey there's 100 items you can catch while fishing and a free pdf of Pirate Palaces

Recommendations Please!

I'll keep this guide updated so please suggest Pirate generators in the comments or on twitter to @DuncanThom

Fantasy Gen Guides - Pirates and Seas | Dark Fantasy | Dungeons | Dungeon Maps | Pets | Pathfinder 1e | Warhammer Fantasy Roleplay