"Grugar is the most disgusting drink I've ever had the misfortune of consuming, and I don't know what it has to do with anchors." - from the memoirs of Lewin Von Treet, Vault: the Land of Stuff and Things
Population: ~800
Founded: 2300 (90 years ago)
If Topside is filled with pirates who enjoy the limelight and have made a business of their villainy, and Broken Compass is filled with pirates who dwell in the mystical and embrace the mystery of the sea, then Grugar's Anchor is filled with pirates who enjoy stabbing, detest sobriety, and indulge in indulgence to an objectively unhealthy degree. Grugar's Anchor is a city that does not sleep, unless it's hungover, and has more murders than the rest of the Arrowhead Isles combined. Walking into the Anchor is forfeiting your well-being in multiple ways.
To live there is to follow a simple set of rules. The first is to do whatever you want whenever you want. The second is to drink Grugar. And that's it. Those are the rules. If you don't like Grugar, you'll more than likely find a knife in your back by morning. If you ask what Grugar is, you'll have a knife in your back by morning. If you find Grugar delicious and can't get enough, you're deemed one of the "lads or lasses," and more than likely find a knife in your back by morning.
It's hard to run a business in Grugar's Anchor. Stealing what one wants is literally the occupation of every occupant of the city, so one doesn't really earn a living by providing services. Still, there are those who are just that insane, or more realistically, just love the people and the life that much.
And when one gets right down to it, there is a lot of love to be had in Grugar's Anchor. Backstabbing is as common as a rainy day in the Isles, but there is a camaraderie and family that forms over time, and sometimes that time is very short. It's a town of scum, villains, and cutthroats, but the people of Grugar's Anchor would have it no other way.
Grugar's Anchor makes use of its location in the Isles as the town closest to both The Fair Way and The Tenth Layer, both passaged to the inner isles and the Siren's Suckhole. Heading west and coming at it from "oceanside" runs ships afoul of sea monsters who dwell in the deep, so threading through the Isles is often preferred. Unfortunately, the pirates of Grugar's Anchor know this fact well. They're known for taking no prisoners and never wasting an opportunity to waste an opportunity. Condemned by the citizens of Topside as wasteful and stupid, Grugar lads and lasses care more about having a good scrap and proving their ships the stronger than plundering riches.
After all, it's not like they pay for their drinks.
This has given Grugar's Anchor a reputation as not only a dangerous city, but also fielding the nastiest pirates in the Isles. If a ship sees an Anchor flag flying, it may be best to simply abandon ship on the spot.
Grugar Brewery - a misnomer since Grugar isn't brewed, but the people of Grugar's Anchor don't care. It's where their beloved drink comes from, and they don't care what it's called. For as much they drink, this brewery pumps out as much of the stuff as some of the more famous rum distilleries in the Isles. The difference is no one outside the city actually drinks it.
Safety Street - sometimes there are kids, and kids oughts be kept safe. So Safety Street was concocted as a way to keep children from being at the mercy of dangerous people. When you're in Safety Street, you're safe, no questions asked. Unless you're an adult. Then the kids may kill you themselves.
Kressent Bay - the harbor in Grugar's Anchor is shaped like a crescent, and some sign makers are poor spellers. This is where the majority of the bars, brothels, and bars stand in the town, and where one can always find a lad or lass looking for a voyage to get into a scrap.
Ol' Bones - Male Human, biggest scrapper in the city and drinking champion
Kittie LaForge - Female Halfling, head brewer of Grugar and suspicious conspiracy theorist
Heel Kart, the Disappearing Ferret - Male Human, the Big Kid on Safety Street, he makes sure people are following the rules and tells on 'em if they don't
Buckles O'Malley - Male Dwarf, captain of the Starless Sky, the vessel with the most scraps won in port at Grugar's Anchor
Faust Lichdenholm - Female Tortle, captain of the Home for the Holiday, a ship known for merciless killings from a distance
Verge the Nerve - Non-Binary Half-Elf, captain of the Helldiver, the ship and crew who haven't failed to navigate The Tenth Layer...yet