With His O'ertaking Wings (d20 Ships and Captains)

 Much of my creative energy has been going to my countries-as-megadugeon, or "megawildernesscrawl", project, a setting I have begun to call Before I Sleep. As I worked on the first draft of my key, I noticed an old pattern. I was sure that if I started to post excerpts from this project, like a kingdom with a little region map and key, it was sure to be outdated almost instantly as I added and changed elements. So for now, I'm going to try to stick to posting the side dishes-- procedures, classes, and fun tables that may be interesting on their own. If you want to see my current draft of the overall setting, warts and all, just message me on the discord or something. 

from Howard Pyle's Book of Pirates

This is a table of notable sailing ships you might find in the big ports, like Danbrag or outside of Hepton. When the player characters have need of transport, the DM should roll two or three times on the table to see who is available to transport them on short notice. If PCs make a habit of traveling by sea, it will feel like a small world indeed. Inspired in part by how much fun it was to write captains for the Sceptre-Shaken World.

d20 Ships and Captains

1. The Renegade, a large sailing ship captained by Willard Last of Danbrag (Bard 1). Perhaps the last honorable captain on these waters, he would rather die than betray anyone on his ship. Crew of 30, stats as merchants.
2. The Dicemaker, a small sailing ship captained by Ronvoine the Rat of Coris (Thief 4). A gambler with connections in the criminal underworld of every port, his ship has several discrete smuggler's holds. 1-in-6 chance in every port that one of his annoyed and dangerous patrons introduces an extra wrinkle into his current job. Crew of 10, stats as brigands.
3. The Grandee, a small sailing ship captained by Terla Goldeneye of Danbrag (Thief 2). A woman of means who made her fortune through years as a porter and thief-finder. Greedy, but with a spine and integrity. Crew of 15, stats as normal humans.
4. The Dare-Treader, a small sailing ship captained by Hidalga Ageda De La Rosa of Phoenix Land (Fighter 2). She has read all the manuals and studied all the knots, and Ageda plans to excel in seacraft just as she has excelled in everything— tireless preparation, careful financing, and a deep well of natural talent. Superstitious as any lifelong sailor, she subtly passes a holy symbol by any prospective passenger for signs of vampirism. Crew of 18, stats as dervishes.
5. The Sexy Woman, a small warship captained by Den Happenstance of Hepton (Fighter 1). A senseless, lecherous drunk, Happenstance cuts as imposing a figure as ever a Heptonian officer ever did. His greatest skill is in taking credit, and his career is buoyed by the thankless work of his second, Half-Dead Jim. Imagines that he is in a deep rivalry/romance with the Atlas's Selvine. Crew of 40, stats as goblins.
6. Impunity, a small warship captained by Branwenn Gayblade of Evardin (Fighter 3). A soggy, vaguely pathetic raider from a family of raiders, she never seems to get any respect. Would kill for a true friend, but would probably betray that friend to make her father proud. Her ship has a subtle ram in its prow, carved to resemble the head of a squid. Crew of 20, stats as buccaneers.
7. The Fishmonger, a small sailing ship captained by Peg Leg Pew of Hepton (Fighter 3). Massive, barrel-chested, small-minded, hard-hearted is Peg Leg Pew. Passengers who play on his pride have an alright time. Those who wrong him are chained to a special chamber in the depths of his ship that floods with high tides. His ship has a rare "cannonne," a deep metal chamber filled with blasting powder and ignited to fire metal bullets and shrapnel. Crew of 20, stats as bandits.
8. Beatrice, a large sailing ship captained by Boska Blackbird of Danbrag (Thief 5). An inveterate scoundrel, Boska is likely to betray or abandon her passengers if there is profit in it. There's a 1-in-6 chance at every port that she'll run into one of her many more powerful enemies. Crew of 30, stats as pirates.
9. The Red Cent, a small whaling ship captained by The Harbormaster of Phoenix Land (Fighter 2). A shadowy figure commonly believed to be some former crusader or insane wanderer, they carry passengers to fund their hunt for a sea creature which has scuttled two of their previous vessels. Crew of 25, stats as berserkers.
10. The Linerunner, a small sailing ship captained by Davriel Karlin of Danbrag (Thief 2/Fighter 1). During a dispute between Danbrag's guild of porters and its constabulary, the port was effectively shut down and the people suffered. Karlin, a smuggler, managed to sneak in much needed food to the porters at risk of his own neck. For this, his station has been elevated from a common chancer to a merchant of means. He retains the common touch (constant over-the-top nautical similes and saying "ahoy".) Crew of 20, stats as bandits.
11. Moonslave, a large sailing ship captained by Sea-Mistress Calbride of Hepton (Necromancer 2). Capable and proper, she was convinced to come out of retirement to sail again. Unbeknownst to her, many of her recently-hired crew are veterans of the finally-slain dread pirate MaClu, and there is a 1-in-6 chance every time treasure is on the line that her boatswain, Tarsal, will lead a mutiny. Crew of 35, stats as buccaneers.
12. Morgana's Revenge, a large sailing ship captained by Rhisiart Newblood of Evardin (Fighter 4). A retired adventurer, Newblood named his ship for an old travel companion of his, a magic-user of no small talent. Fair and open-minded, he is nevertheless susceptible to the vices of his former profession: foolish risks, forgetfulness, and extremely poor judgements of character. Crew of 20, stats as nomads.
13. Atlas, a longship captained by Selvine of Danbrag (Fighter 3).Those who get to know Selvine find her to be a true renaissance woman. Her interest is in exploration, and her ship is well-stocked for long voyages and many surprises. Reduce the effects of weather on this ship by one step. Crew of 90, stats as merchants.
14. The Starfish, a large warship captained by Clever Cefni of Evardin (Rogue 4). Works under a letter of mark for Danbrag, mostly robbing or capturing Heptonian vessels. Makes a little extra money getting passengers and cargo where it needs to go. If hired in Hepton, he is there under a flag of truce and to exchange prisoners. His greatest wish is to capture and unmask the Red Avenger. Crew of 40, stats as pirates.
15. The Shark, a small sailing ship captained by Hema of Danbrag (fighter 2). The leader of an unsavory crew, she seeks revenge against the woman who cut off her good left arm in a battle almost two decades hence— one Calbride of the Moonslave. Her ship moves with surprising quiet through surprisingly shallow waters. Crew of 15, stats as pirates.
16. Medusa, a longship captained by Osk Balborgsdottir of Thognheim (Fighter 3). She and her crew of old salts are under a deep curse, and never can reach their home city. They eat lotus flowers which give them visions of their homeland. If rolled in the port of Thognheim, no it wasn't. Crew of 80, stats as veterans.
17. The Red Tide, a large sailing ship captained by Lady Craven of no claimed home port, but by the designs of her ship and style of her attire it must be Hepton (Thief 4). Though affecting the persona of a vain fool who loves only baubles and petty rumor, Craven is a vigilante and master of disguise, and if some injustice has been done at her latest port (1-in-6 chance) or if the PCs are wronged by some tyrannical act, she will don the mask of the Scarlet Avenger to set it to right. Crew of 25, stats as thieves 1.
18. The Northwind, a small warship of sleek design captained by Thorsic of Bes (Fighter 3). He despises the chaotic and oppressive mercantilism of Danbrag, and leads a fleet of one against them. His ship has been enchanted with the ability to submerge itself until only its crow's nest is above the water, allowing for great stealth at night. If hired in Danbrag, he is disguised as Captain Jack Stormwrack of The Reliable. Crew of 30, stats as berserkers.
19. Seaward, a small sailing ship captained by Kendris of Hepton (Magic-User 1). Tricked into the sailing life by his more ambitious sisters to get him out of the way, Kendris believes he is ready for anything life throws at him. His crew fervently attempts to save him from his own undoing. Crew of 13, stats as merchants.
20. Fancy Dancer, a small sailing ship captained by Much of Hepton (Fighter 4). How a barking mandrill-like monster such as Much gained a ship and how she managed to win the zealous devotion of her crew is unknown. A black-hearted bunch, they are not above press-ganging those who seem useful. Crew of 15, stats as neanderthals.