I was just at the library this afternoon and took my usual detour through the Sci-Fantasy section looking for something different. No spaceships, no magic swords, no “What if Hitler won” stuff. I decided that I wanted what I determined should be called Pirate Fantasy. I want a long running series of pirate fiction with strong central pirate antagonist. Am I SOL or just can’t find what I want?
I’m not very well read in fantasy, but there were pirates (sorta) in Robin Hobb’s Liveship Traders trilogy.
Are you looking just for pirates, or would nautical fiction serve?
Check out The Pyrates by George MacDonald Fraser.
It’s a one-off rather than a series, but get yer mitts on George MacDonald Fraser’s The Pyrates, a glorious send-up of every pirate movie and book there ever was. As far as more “serious” books go - I put “serious” in scare quotes because they’re mostly just tremendous swashbuckling fun - books go, try Rafael Sabatini: his books, Captain Blood among them, are pretty much the source material for every pirate movie ever made: try also his The Sea Hawk or The Black Swan. In a similar vein there’s also Jeffrey Farnol: Black Bartlemy’s Treasure, Martin Conisby’s Vengeance and Adam Penfeather, Buccaneer are recommended. Farnol and Sabatini’s novel’s are a good few years old, but still can’t be beat for classic pirating: I know Sabatini’s still in print; dunno about Farnol, but they’re pretty easy to track down.
You can always move to the Watchmen universe. 
John Gregory Betancourt wrote several fantasy novels involving pirates back in the early 80s. (He once described on as “Pirates fighting giant ants.”) If you can’t find them, you can probably ask him at Wildside Press (he’s publisher) if he has any copies for sale.
Hugh Cook’s Chronicles of an Age of Darkness is a ten-book series with a heavy pirate component, particularly in book 2 and book 4. The ten books are:
- The Wizards and the Warriors
- The Wordsmiths and the Warguild
- The Women and the Warlords
- The Walrus and the Warwolf
- The Wicked and the Witless
- The Wishstone and the Wonderworkers
- The Wazir and the Witch
- The Werewolf and the Wormlord
- The Worshippers and the Way
- The Witchlord and the Weaponmaster
Each book is written in a totally different style. The second book is played for laughs, while the fourth one is more of a straight-up adventure story with a touch of romance. All ten books in the series have tons of action and furious pacing.
(Beware that the American publisher released several of the books under alternatre titles for some strange reason. Book 2 exists in America as two volumes, The Questing Hero and The Hero’s Return. More information here.)
I should also mention that Fraser’s Flashman series is excellent for 19th century pirates: Flashman’s Lady has Flashy in Borneo pitted {with the aid of Rajah Brooke} against Malay pirates - captained by an old Etonian parvenu who cheats at cricket and steals wives; Flashman And The Dragon has Flashy in China {helped and hindered by Frederick Townsend Ward} unwittingly running opium up the Pearl River, not to mention afoul of a nest of Chinese pirates. Best of all, though, is Flash for Freedom, in which our hero, fleeing a possible murder charge, reluctantly runs African slaves from the Ivory Coast to the Americas, under the command of the abominable Latin-quoting former Oxford don turned pirate **John Charity Spring and one short jump ahead of the US and British navies. Flashy also seems to have been shanghaied - at the instigation of a clergyman’s wife turned opium trafficker - from a dockside Hong Kong brothel to Australia and the Pacific, but that instalment of his memoirs hasn’t turned up yet…
How about Robert Louis Stevenson?
I’m reading Tim Powers’s On Stranger Tides right now. You couldn’t get more piratical.
after reading it a bit more But it’s not very good.
I write pirate fiction, but I can’t link to it here.
…it’s Arrrgghhh!-rated. 
Well, I liked On Stranger Tides quite a bit. Although Tim Powers didn’t produce a string of pirate novels, most of his other stuff is also excellent.
I ditto that. I really liked it, too.
My NaNoWriMo novel last year was pirate-centric. My novel this year is less-so, but still a sequel to the original. Willing to send you a copy if you so desire.
I’ve never read any of his other stuff, but I’m finding his writing style to be a bit lacking in finesse. Or maybe it’s the way he has jammed in so many nautical terms to make it clear how much research he has done. I don’t care about nautical accuracy, I want a story full of likeable characters having a fun adventure, and I’m only barely getting that at the moment.
Having said that, I’m only halfway through yet. It may pick up.
Indeed I am. Email is in my profile.
You ain’t gonna get that from Tim Powers. The adventure may be fun for the reader, but it sure as hell isn’t fun for the characters. Most of whom aren’t likeable. Hell, has he ever had a novel where the protagonist didn’t
get physically maimed in some way?
(adding spoiler tags just in case)
Oh, and William Hope Hodgson wrote a number of stories whose protagonists are vaguely piratical. I certainly wouldn’t call it a long-running series, though.
Oh yes, people still write pirate fiction. And better still, pirate fantasy fiction. Jolly Roger and Dragons and its sequel, The Treasure of Dragon Island, are just such a pair. Rooted solidly in the early 18th century, with Jamaica, Tortuga and other such genuine pirate locations, and with mention of the historical pirates such as Kidd, Teach and Rackham, there is still the sort of elements worthy of a Burroughs novel, lost civilizations, forgotten islands, monstrous beasts and, of course, humor and a bit of romance.
All too often, these sorts of novels can only be found on Kindle and Nook, but they are there at least. The biggest problem is knowing what to look for if you want a general catagory rather than a specific title or author.