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Not so much "nautical shenanigans", but a rec nonetheless:

by

"Rocking the Boat" and "In Enemy Waters", both by DerLaCroix on FFN? The second is a sequel to the first and I don't believe it's complete.

It's not a major focus, but has some Harry-at-sea content. Harry and Hermione go off on his family's sailboat after the war in JackPotr's , but I don't remember anything else about it.

I'll second the recommendation for The Sea King; it's quite good. I've read a couple of others whose titles I can't come up with. In one of them, Harry applies to an elite school that conducts classes on a ship at sea while touring the world. In the other one, Aurora Sinistra more-or-less shanghais him into a summer "program" in which students man a ship for her, doing salvage and privateering (IIRC), which is how she supplements her income as a professor. That's the one that's most likely to have hijinks - it's rather cracky, with Draco and his bodyguards assigned to the Black Gang. Crabbe and Goyle express particular interest in Sinistra's promise of "rum, sodomy, and the lash."

In the other one, Aurora Sinistra more-or-less shanghais him into a summer "program" in which students man a ship for her, doing salvage and privateering (IIRC), which is how she supplements her income as a professor. That's the one that's most likely to have hijinks - it's rather cracky, with Draco and his bodyguards assigned to the Black Gang. Crabbe and Goyle express particular interest in Sinistra's promise of "rum, sodomy, and the lash."

That one is one of Rors’ Odd Ideas:

On 10/24/2021 6:32 PM, Jon K wrote:

?As the title says, I have a jones for the Wizarding World at sea. Hit me with your recs! I’ve already torn through Wizards Fall, and I crave more nautical shenanigans.

-Snag

Sent from my mobile - please excuse my typos.

I can't think of many, but there are a couple.
In no particular order


Rocking the Boat
By: DerLaCroix
Harry is left with the Dursleys just after his godfather had died. One thing leads to the other and Harry is fed up with being a puppet. He breaks free and finds help. And boy, does he start rocking the boat.
Rated: Fiction M - English - Adventure/Romance - Harry P., Hermione G. - Chapters: 33 - Words: 245,784 - Reviews: 3,707 - Favs: 9,924 - Follows: 6,771 - Updated: Oct 2, 2012 - Published: Feb 5, 2010 - Status: Complete - id: 5721324

Harry Potter and the Shipgirls




The Sea King
By: Doghead Thirteen
Nineteen years ago, Harry Potter put paid to Voldemort at Hogwarts; now it's nineteen years later and, as the diesels hammer on, a bushy-haired girl is still searching for The-Boy-Who-Walked-Away... Oneshot, Deadliest Catch crossover.
Rated: Fiction T - English - Words: 5,361 - Reviews: 290 - Favs: 1,756 - Follows: 416 - Published: Oct 28, 2011 - Status: Complete - id: 7502511


Runaways
By: Ravengrad
Harry's had it and Hermione receives some startling news.
Rated: Fiction T - English - Romance/Family - Harry P., Hermione G. - Chapters: 7 - Words: 47,241 - Reviews: 388 - Favs: 2,398 - Follows: 739 - Published: Feb 22, 2013 - Status: Complete - id: 9037417


Escape
By: JackPotr
A little something that has been bouncing around in my head. Has the whole range of emotions and starts after Final Battle and changes the whole Epilogue. Definitely Harry/Hermione
Rated: Fiction T - English - Angst/Romance - Harry P., Hermione G. - Chapters: 4 - Words: 39,442 - Reviews: 313 - Favs: 1,473 - Follows: 579 - Updated: Sep 7, 2013 - Published: Jun 6, 2013 - Status: Complete - id: 9364319

I almost forgot, Marquis-Black's "Dark Wars" series features airships like in the Spelljammer series, or to a lessor extent Final Fantasy IV.

Basically sailing ships in the sky.

That makes sense; it is his kind of story. There are a lot of stories I recall reading that are one or more chapters of someone's one-shots and potential/abandoned starts collections. I have over 30 such collections in my reading list, one of which has 277 chapters, so there are a lot of things I have trouble finding again. Odd Ideas has almost 200 chapters, itself.