D&D 5E Your Players Stole a Pirate Ship and Made Way for the Seas. Now What?

Avast, me hearties! 'Tis time to set sail for the Isle of Dread!

I've this fine map to some booty taken from the scurvy dog who were captain. Iff'n it don't pan out, then we'll turn privateer and collect some bounties on ships tradin' wit' th' Scarlet Brotherhood.

Yo ho!
 

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Kid Charlemagne

I am the Very Model of a Modern Moderator
Another great resource for pirate and sea-based games (especially if your ships start running into the 16th/17th century type ships) is Corsair from Adamant. It's 3.5, although it looks like it might have been updated and expanded for Pathfinder, too. I used this as the go-to sailing rules for my game, after trying out many other 3.5 and 3.0 variants.
 

Scarbonac

Not An Evil Twin
What sorts of challenges would you throw at your party? Or published adventures you like for this sort of thing?

Pirates. Pirates.

And Pirates.

Sea Monsters (sea-serpents, plesiosaurs, giant squid/octopus, sea-dragons).

Lost Spelljammer ships/culture remnants on desert islands.

Atlantis/Lemuria/Mu-based encouters.

Lovecraftian cults.

THE ISLE OF DREAD -- I added a lot of the other elemnts to the base IoD module and it became my main campaign -- sea-faring, tentative space-faring toe-dips, fighting slave-taking pirates, dealing with dinosaurs, recovering lost space-dorfs in magical stasis (which I gave an Egyptian flavor to rather than the standard "Gimli in Space" treatment), weird tech (a little Gamma World a little Lum The Mad), forming alliances with Islanders against pirates and unholy zombie cultist cannibals...
 

billd91

Not your screen monkey (he/him)
Since Skull and Shackles and Savage Tide have both already been mentioned, I'll bring up Assassin's Creed 4 - Black Flag. While not very D&Dish in a number of ways, it's got some worthwhile inspiration in locations, ruined temples, and secret societies at work. And, of course, it has NPCs inspired by the Golden Age of Piracy, which you can read something about here:
http://en.wikipedia.org/wiki/Golden_Age_of_Piracy
 
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Mistwell

Crusty Old Meatwad (he/him)
I've never read Savage Tide, but I think (?) I own those Dungeon magazines, and I've remember hearing good things long ago.

So what are people's general impressions of that Adventure Path?
 


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