D&D 5E Make a pirate island come alive (Forgotten Realms)

Nebulous

Legend
I'll just throw this out there, it was a magic item I used in 2e that a pirate captain had. The knot of winds. It was a knotted rope that could be undone one at a time if a ship was stuck at sea with nothing in the sails. In my scenario though the PCs were kicking his ass and his cronies on land, and the captain rips the whole knotted rope down the line and it unleashes a typhoon force wind in the middle of the fight.
 

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If we're talking taverns, might I suggest serving something along the lines of the El Draque, from the 16th century:


Essentially, rum, lime, sugar, mint, with the rum infused with a local medicinal tree bark. I've made a version of it (I have a Caribbean herbal infusion, though it does not contain the same bark) and it's actually pretty tasty.
 


Eltab

Lord of the Hidden Layer
A fellow offering to give swimming lessons for a fee. If you make him cantankerous, he will just throw you overboard. If you treat him like a teacher / student, and take a week of lessons, you can swim on the surface in normal conditions. You also (accidentally) learn to swim underwater and hold breath for a bit longer than the basic rules allow.
 

generic

On that metempsychosis tweak
Well it's not a person per say, but I did make a set of items to help out with a pirate theme.

As for a location:
The Hookline. A half sunken tavern-ship that hosts a partially submerged bar where meetings between aquatic and air-breathing folk are frequently arranged, due to it being equitably hospitable (if slightly uncomfortable) to both parties.
This is great! I'm totally using this idea in my Saltmarsh-esque campaign region!
 

Another source of inspiration might be China Miéville's novel, The Scar. If I remember correctly, it featured a floating city of ships. They weren't wrecks, I think, but they were definitely linked together. Lots of shenanigans happened there.

As for a specific recommendation, there is a giant octopus/kraken/sea monster who hangs out beneath Shipwreck Island. It is in thrall to the pirate queen. Or an ally. Or she's in thrall to it. Whatever it is, it should have tentacles (both literal and figurative) that can create entanglements all over the island. Perhaps it helps move the island and keep it safe, but it demands a blood price. Many on the island may not even know about it, but there are grim rumors of midnight rites and mysterious disappearances.
 

Ancalagon

Dusty Dragon
Another source of inspiration might be China Miéville's novel, The Scar. If I remember correctly, it featured a floating city of ships. They weren't wrecks, I think, but they were definitely linked together. Lots of shenanigans happened there.

As for a specific recommendation, there is a giant octopus/kraken/sea monster who hangs out beneath Shipwreck Island. It is in thrall to the pirate queen. Or an ally. Or she's in thrall to it. Whatever it is, it should have tentacles (both literal and figurative) that can create entanglements all over the island. Perhaps it helps move the island and keep it safe, but it demands a blood price. Many on the island may not even know about it, but there are grim rumors of midnight rites and mysterious disappearances.
I came here to mention The Scar as well. What a book!
 

Matthew P.

Villager
The Seachest-
A small shop in what used to be a bunk room. The hammock bunks are full of a chaotic mix of junk, jewelry, and gear. Everything seems to have just been tossed there, but the owner insists there's an organization underlying it all. She and an aquatic friend gather stuff from derelicts and wrecks and sell it here. Probably a few magic items in there if you look hard enough. If you want something, it must be worth quite a bit.

Squid's Galley-
A long ship strung up between a few broken masts. It creaks and wobbles a bit, but is home to Squid - the best damn cook on the sea. He serves up any sort of seafood you can imagine - perhaps even a few sentient ones. He's served on countless ships, and survived a few sinkings. Good for advice, either how to fend off scurvy, or how to get information out of someone in particular.

Thank you! Definitely gonna use Squid's Galley!
 

Matthew P.

Villager
Another source of inspiration might be China Miéville's novel, The Scar. If I remember correctly, it featured a floating city of ships. They weren't wrecks, I think, but they were definitely linked together. Lots of shenanigans happened there.

As for a specific recommendation, there is a giant octopus/kraken/sea monster who hangs out beneath Shipwreck Island. It is in thrall to the pirate queen. Or an ally. Or she's in thrall to it. Whatever it is, it should have tentacles (both literal and figurative) that can create entanglements all over the island. Perhaps it helps move the island and keep it safe, but it demands a blood price. Many on the island may not even know about it, but there are grim rumors of midnight rites and mysterious disappearances.

Like it! Thanks!
 

Eltab

Lord of the Hidden Layer
One shady fellow has a peg leg. If you tread on his business turf, he will invite you to his office for a drink and a nice chat to smooth out the misunderstanding. If the PCs do not bend to his will, he will shuffle around to put the peg leg up and point his 'foot' at the PCs. "Ach, my bad leg, she pains me." He actually has a one-shot Lantan cannon (loaded with buckshot) in the peg that he will try to discharge into the group. Use Eldritch Blast or a dragonborn breath weapon for the mechanics. If the peg leg got wet recently, the powder will not burn but there will be an audible 'click' when he tries to set it off. His cohorts and subordinates recognize the quoted line as a verbal warning.
 

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