Ideas for making a quirky city/settlement?

[MarkVIIIMarc]

I'm looking for ideas on how to make a small island settlement quirky enough to be different than the usual town.

A party I DM should spend a couple sessions in or near a town using it as a base while clearing a dungeon. The town is fairly isolated on an island and I'm considering giving them a military based on their navy. Something odd like everyone wants to be a sailor no one wants to be a soldier or marine.

In a previous session the party encountered a group of less civilized nomadic people who were slightly based off native Americans but had all their men except one, a pc for a player sitting in, killed by the bad guys. So that's been used and I think pretty successfully.

Thanks for any suggestions.

[Drakkoniss]

It might be useful to clarify precisely what you consider to be "the usual town."

You are certainly dealing with interesting themes, from what you've described, but it would seem wasteful to offer suggestions that might seem cliche or over-done to your tastes. (Though I would suggest finding a reason for all of them wanting to be sailors that is based in their culture, if you're going for that. Perhaps have the city devoted to a sea god, or something of the sort? Maybe make them have a founder who was an hero famous for his sailing skills?)

[Sigreid]

Everyone believes that names have power and will go to great lengths to not call anyone by name in public. It is a sign of the greatest trust for someone to whisper to you their name.

[Laserlight]

I'd flip the script. Make the settlement inland. There are no boats, the people don't fish at all, they totally shun the sea. They raise cattle, farm, don't resemble islanders at all.

Make it a mystery. Quirky indeed..

I vaguely recall that part of the New Zealand coast was deserted when Europeans arrived. Apparently the area had been hit by tsunamis and the surviving Maori had moved inland and uphill. I also recall hearing about possible evidence of a wave 200ft high.

[Mercurias]

Have the town consider sailors and fishermen to be the epitome of heroism because the town is entirely dependant on the sea for sustenance?

[Trustypeaches]

Maybe the settlements is underwater, populated by triton, sea elves, and merfolk. The above-surface territory is just their farms and other things they can't utilize underwater.

[VonKaiserstein]

Due to the tremendous amount of trade with various shores the village does, all local currency is handled by ship-script (notes redeemable on the ship's reputation) or a certain variety of seashell. Only money changers are remotely interested in your gold, silver and platinum. Stretch it out, and you can get your party excited about finding a chest of seashells. Make a big deal about it when they arrive and in the initial sessions, but don't when they leave.

Enjoy the look on their faces when they try to pay the next town in their huge wealth of shells, and realize they have to go back.

Concurrently, you could have the head of town live in a castle- a sandcastle. A magically held together sandcastle, where criminals are buried in their necks in the walls for a period of time, internally for minor offences, and externally for serious offences. Alter most oaths to revolve around sand and sea.

Huge bonus points if you can get your BBEG named Anakin without the players realizing what you're doing.

[Man_Over_Game]

The "island" is actually a floating collection of shells and husks from sea monsters. They pride themselves on their ability to do battle against monsters and often trade goods with adventurers and merchants. The island shifts in position and travels to new areas every few months/years, with the help of their native Storm Sorcerers, who seem to be more common than usual on the island.

[Vogie]

Some ideas:

There is what used to be a land bridge that would have connected the island to the mainland, but it's clearly cut off by a non-natural means, and while there is clear evidence of attempts of building a bridge on the mainland side, there's nothing on the island side.
The island itself is the back of a massive living being, so it moves around in a seasonal pattern, albeit verrrrrry slowly. The islanders don't mind, as they can never overfish the waters, and defend both the information and the island-being with great vigor.
The town doesn't seem to have a clear reason why it exists externally - the land isn't great, it's not really on a trade or war route, everything they have can be gotten cheaper elsewhere. It turns out the island itself was created as a supermax magical prison, and the town originally was "founded" as a 'company town' to take care of the wardens, not dissimilar to how Castle Rock exists mostly to support Shawshank Prison in Stephen King novels and the Hulu series of the same name. Generations have passed, and life is tough in the town prior to the adventurers arriving.
Similar to the above, but instead of a prison, the town is based around a natural feature that inclines residents to not leave. It could be healing waters, Eureka-Springs-Style; it could be a Fountain of Youth, allowing the residents to potentially live forever, but chemically castrates them so they can either reproduce OR be immortal, which explains why the population never grows; it could be some sort of mineral or leyline that makes things easier only in that area (similar how most of Wakanda's technology only works in Wakanda due to the amount of vibranium in the ground).
The town used to have a bustling economy, but everything has moved out, yet they still seem to be doing above average. It turns out it's similar to Lakeside, from the American Gods novel, which periodically makes human sacrifices to a minor deity to make sure their little town stays in place.

[rahimka]

The whole place is a series of interconnected floating buildings and walkways (maybe its mobile and they can detach and relocate to a new island every few years). Soon after arriving, the party has to chase a thief (or a few thieves) across this confusing layout
Locals are REALLY into their maritime sports which include diving (high dives off the nearby cliffs for style and depth diving for pearls in the lagoon) and wrestling with local water-creatures (constrictor snakes, crocs/gators, sharks, etc...)
They have a tradition of settling disputes with surf competitions. Wouldn't you know it, somebody in the party pisses off the wrong person and gets challenged
The local temple / favorite deity is shark/snake/octopus themed and the priests, who have a very public role, give off a REALLY creepy or aggressive vibe