"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."
A guide to random tools for fantasy adventures and campaigns on the seas. Generators for everything pirates, swashbuckling and seafaring.
The seas are a favourite place to adventure for many rpg groups. Exploring islands, battling sea monsters and hunting pirates.
Adventurers with access to a ship and maybe a crew have the freedom to go many places, and a sense of control.
There is also a generator Guide for Taverns.
Star of Heawold: This warship has a battle-scarred hull, and is pulled by a team of giant sharks. The ship's commander is a perceptive man named Ealhmun, who is hunting the sea monster which killed his family.
From the Fantasy Ship Generator at donjon.
Whether you're pillaging, pirate hunting or exploring the seas, ships will be involved.
"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."
From Pirate Character Generator at springhole.net
Darby "Nightmare" Law and Cassie "Yellow Teeth" Seymour are fearsome Pirate Names from Fantasy Name Generators. While the Pirate Name Generator at 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.
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."
There are more to mariners than pirates.
Add a Tattoo from Enead Games, such as a "faded tiger on the upper thigh from a tribal initiation".
Personalise with something from the Charm Generator at Chaotic Shiny Generator like "A small gold charm with a hearth and two serpents on the front and the same on the back".
To give a small bauble or memento for each character there are Sea Trinkets at Chaos Gen
Alternatively they might carry one of 100 Aquatic Items from Dnd Speak like "Shell Shield: Shield made from the shell of a giant clam or turtle. Standard stats at half weight.". Or have them catch something interesting from 100 Things You Pull Up From a Casted Net at Sea.
"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."
From the Weather Forecast Generator at Chaotic Shiny
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.
You might want one of 100 Sea Travel Events from DnD Speak 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 a Beach Encounter 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."
Last is a list of 1d20 Sea Encounters from 2 Minute Tabletop
In the abyssal waters of a black, gloomy sea lies what remains of the Cordelia, a ship potentially lost during a fight with pirates hundreds of years ago. She's in a rough, but decent shape, although damage at the hands of the sea starts to appear more and more. The barren depths aid in her preservation, but she's in the company of various aquatic beings who see her as their home now. They're a calm bunch in the safety of her waters. They're new inhabitants of a home lost to the tides and time.
From Shipwreck Descriptions at Fantasy Name Generators.
To add detail to your island add try 100 Uncharted Islands (free/pay what you want) PDF at DM's Guild. 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."
Watabou also has Perilous Shores which generates coastal and island maps.
For something nearer civilisation try Pirate Coves from Fantasy Name Generators such as "Skeleton Lagoon" or "Port of Booty". Perhaps you'll visit Harbor such as "Hasshaw Landing" or "New Meadow Wharf
Either might contain a Treasure Trove from Chaotic Shiny. 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.
For Taverns there is a Random Inn and Tavern Generator at donjon producing the "Cursed Axe". And also a Rand Roll Generators Guide for Taverns.
Then there is a a free pdf of Pirate Palaces
If you are after island map tiles I found a pdf, Tropical Islands - Map Tile Set.
I'll keep this guide updated so please suggest Pirate generators in the comments