After a few days of sailing across the sea, the skyline of Rogueport soon came into view for the passengers aboard the ship.  A murky brown outline thinly spread across the estuary, a small river flowing out into the sea from the right side of the town.  The salty sea air rejuvenated both James and Koopin, as they hopped off onto a rather different-feeling dock.  Compared to the cheerful easygoing Toad Town, this town was entirely the opposite.
Cracked streets, cloudy roofs, rough-shodden travellers with ill-wearing suits and scars to match their perpetual frowns.  The dock itself was a stonewalled cove of crates and murky ships, with the town itself up along a stone stairway.  Various creatures passed them by, mostly rough well-travelled toads and bob-ombs.  James also noted the bob-ombs to be a lot more corsair-like, with dewrags and bone-like wheels replacing the usual clockwork key in their backs.
	"Welcome to Rogueport," said Koopin firmly, "a town of a thousand years of ruin and desolation, all culminating together into the gateway to the sea you now see before you."
	"Huh...pretty interesting so far, certainly not as happy-shiny as Toad Town is."
	"Just between you and me," murmured the koopa, "this place is a haven for thieves and criminals.  That's why it looks like this.  The Robbo Gang runs the east side, and the Pianta Syndicate runs the west side.  You'll notice it when we get into the town proper."
	"Alright."
Climbing up the stairs to enter the town square, James already felt a whole new change of personality within the place.  A seedy inn with a bar front to his right, a store with the smells of many foods coming from it to his left, with a badge store built above it strangely.  Merchants with wares sat on street corners, with their produce displayed upon moth-eaten rugs.  What really caught James' eye however, was the gallows in the very centre of the town, a morbid structure with a lonesome noose swinging in the sea breeze.
	"Hhhahahaha, holy shit that is dark."
	"Yeah...not a nice place."
	"You kidding, this place is awesome!"
	"H-huh?!"
	"Dark grimy stores, the smell of crime, punks and mobsters everywhere you go, the subtle hint of death and murder...this place.....hah, feels like home."
	"...I don't think that's something to be proud of James."

Koopin grimaced slightly up at FG's expression, which turned somewhat dreamlike as he sighed with content.  Walking through the square until he bumped slightly into a rough-looking toad, he was met with an angry:
	"Hey, watch where ya going!"
	"Hey fuck you pal," said FG, "you got eyes dontcha?!"
	"Yeah but looks like YOU don't."
	"You wanna start something?!  HUH?!"
The raptor spread his arms aggressively, smacking his chest much to Koopin's silent outrage.
	"Come on short round, come at me!  Just try it!"
	"...forget you.  Weirdo."
The toad backed down by simply turning away in disgust, not in the mood to pick a fight with the stranger as FG turned back to Koopin with a grin.  The koopa was not amused.
	"Wh-what the heck James?!"
	"Hey-ey-ey, don't lecture me about my anger, I wasn't angry that time.  That was just me asserting myself.  You cant look weak in a place like this or they'll beat you up."
	"Asserting?!  You were asking for a fight!"
	"Koopin...look.  I know exactly what kind of place this is.  Trust me, I know how this place works already."
	"Oh really?"
	"Yeah."
Koopin merely crossed his arms and rocked on his heels surreptitiously.
	"Alright...prove it.  What can YOU tell me about Rogueport that I don't already know?"
	"...well...firstly."
The raptor turned towards the merchants at their side, pointing at one rather smart-looking bright-eyed toad standing beside a rather poorly-looking desperate koopa with haggard eyes.
	"That guy is shifty as hell, his clothes are too neat to be an honest guy so he's either a scammer or he has no idea where he is.  Either way, he's gonna charge you high for shitty goods."
	"Ahhh huh."
	"That guy on the other hand, he's an honest dude."
	"...the scruffy-looking koopa?"
	"Yeah!  He's desperate sure, but he got his stuff fair and square.  His clothes are second-hand, he guards his stuff very carefully showing how much they mean to him, and he doesn't even try to smile.  Nobody in a place like this should smile."
	"Why not?"
	"That's a sign of good wealth and arrogance.  Two things that'll get your ass killed here.  That guy, the toad?  Trying way too hard to smile, that's a scammer's smile."
	"...alright.  Not bad so far, but what about the dangers?"
	"Hah, dangers?"

At that moment, a bandit passed near them with a small shove and a murmur of pardon.  But he barely got past a few inches before James grabbed his arm hard and pulled him back.
	"Give it back," he growled.
	"Wha-HEY, get offa me!"
	"Not until you give back my money bitch."
	"Wh-what money, I didn' steal nothing!"
	"So you were just groping at my pants because you like me then?  You're either a thief or a pervert, which one should I call you when I take your ass to jail?"
The bandit stammered slightly before looking nervously back and forth, groaning with frustration as he pulled out a small bag of James' coins.
	"A-alright alright, here, jus' lemme go."
	"Thaaaaank you."
The raptor shoved the would-be thief away before turning back to Koopin, putting his money back into his satchel.  He quickly remembered however to close it tightly with its straps, fastening it securely.
	"To be fair that was my fault, I shoulda locked this thing when I got off the boat but hardly anyone steals from me."
	"Until you arrived here," said Koopin.  "How did you know he was stealing?"
	"Growing up in city slums, you tend to know what it feels like to have someone's fingers hooking into your pockets or bags.  There are some less obvious scams however...like that one."
He pointed over towards a rather strange-looking character, who looked somewhat like a giant pear with huge boxing-glove like hands, a big wobbly nose and hair like a small palm tree.  James was rather unsure of him at first, but he could easily see by the intrigued expression, loud colourful shirt and youthful eyes that he was a tourist.
	"Who's that?" asked FG.
	"...I dunno, just some tourist."
	"No no I mean...WHAT is he?"
	"OH, oh he's a Pianta!  They come from Isle Delfino way down southeast.  Real nice guys...except for the Pianta Syndicate over on the west side of town.  Real cold guys, professional criminals and all that, basically run the whole of west Rogueport."
	"Heh, right.  Oh, oh, hold up, here they come."
A small group of ragged-looking kids comprised of toads, shy guys and koopas ran up to the pianta with thick cardboard shields, clamouring around him excitably as they padded thick cardboard against the tourist's pantlegs.
	"Awwww look," said Koopin, "they wanna play knights with him with cardboard shields!"
	"And thieves too!" said James.
	"H-huh?!"
	"This is one of the oldest tricks right here.  The kids put cardboard against his legs, making him feel it pushed against his body.  That way he won't feel the tiiiny little fingers slowly reach inside his pocket and...bam."

He pointed towards one kid at the pocket region, the little shy guy adorably sneaking out the guy's wallet before they all started making more noise and shifting it between their hands unseen.  Soon they ran off, the tourist none the wiser until he would next check his wallet, a foolish smile eagerly upon his face.
	"Awwww that's mean!" said Koopin.  "We better tell him, an-"
	"No no, don't.  He won't get it back if he goes to the cops or so...I got a better idea.  Didn't you say the Pianta Syndicate was west of here?"
	"Uh...y-yeaaaah?"
	"Come on."
The raptor for once lead the koopa, as they made their way towards the west side of town.  A stark difference from the middle road of slum-laden Rogueport, the west side was somewhat more well-built with wealth.  Finer houses with several stories, a small park with a garden and fountain feature, as well as a proper general store and what appeared to be a gambling arcade.  James also saw a train station through an alleyway heading north, with a rather shady-looking pianta standing next to the gambling den, entitled "Pianta Parlor".
The pianta standing at the front of the parlor was yellow, with a very fine-looking suit above his leaf-shaped shorts and small black bifocals, standing like a bouncer.  Before Koopin could even stop him, James walked up to him and asked:
	"Scuse me man, you in charge of security round here?"
	"Yeah," said the bouncer, "why you ask?"
	"Well, I just saw some guy get his wallet stolen by a couple of kids, one of those cardboard kid gangs yanno?  And I thought it best to tell you guys rather than someone useless like the cops."
	"Why you wanna tell me 'bout it huh, whutchoo think I am, sum kinda neighbourhood watch?!"
	"...aren't you?  I thought this was like the Pianta Syndicate, like an embassy of some sort?"
	"Embassy?!  Whut kinda operation ya think we're runnin' pal?!  Why dontchoo-"
	"Rocko."
A head peeked out from the Pianta Parlor door, yet another yellow pianta with black bifocals and a fine suit.
	"UH, T-tony, I wuz jus'-"
	"Whut wuz dat abou' sum guy who got robbed?"
	"Some guy up there," said FG, "pianta who just arrived off the boat got mugged by some kids but he hasn't realised yet.  I thought this was like an embassy for you guys, right?  The Pianta SYNDICATE?"
	"...yeah."
The one named Tony stepped out the door and nodded surreptitiously.
	"Dassit...an embassy of sorts.  Rocko, head inside, I'll deal wi' dis."

Rocko was unsure, but soon he headed inside as Tony took his place, nodding firmly with hands clasped before his belly.
	"Sorry 'bout dat, he's new, not exactly got it all up dere yanno so's we just hire him fer muscle."
	"Hah, that's okay."
	"So, whut's goin' on here?"
	"See that pianta across the way, near the inn?"
	"....yeaaaah?"
	"Well some kids with cardboard took his wallet, and I thought rather than whine to the police who'll do jack shit, I thought you guys could help him out, yanno, set him on the right track, get his wallet back or something.  You got more power than just some cops, right?"
	"Heh, right, cuz we're an embassy as you said."
	"Exactly!  So uh, yeah, just wanted to tell you that."
	"No problem, an' thank you fer informin' us of this delicate situation responsibly.  We'll be sure to help out our fellow Delfinian soon enough."
	"Good, glad to hear it.  You have a good day now."
	"Heh, you too."
Cautiously taking Koopin away and around the corner, the raptor grinned smugly out of shot from the pianta mobster to wink at his fellow traveller, who was merely gawking with shock.
	"H-how...you...did you just walk up to a mobster and mistake him for a DIPLOMAT?!"
	"Well yeah...I mean clearly they got the run of the town here and they'll help that guy way more...right?"
	"B-b-but you don't just WALK up to criminals and give them the time of day James, what if he did something to you?!  What if he like, stabbed you or knocked ya out and threw you into the sea to sleep with the fishes?!"
	"Koopin, mobsters operate like any other business.  They got enough class in them to know that if you address them with a polite tone and business sense, then they'll appreciate you.  They're criminals sure, but they're not PUNKS, like those guys over there."
James pointed over towards the east side of town, guarded by some extremely rough-looking birds with spears tightly gripped in their talon-shaped claws.
	"I get that," said Koopin, "but seriously, please be careful."
	"I thought I told you that I grew up with gangsters Koopin.  I know all the ins and outs of how they work, trust me."
He put his arm around the koopa's shoulders, pulling him closely with a smooth grin.
	"You stick with me, and I'll see you through without a scratch."
	"Heh...well...when you put it like that, I GUESS you know more about these things than I do."
	"That's the spirit...now let's go find this Kuribo guy."
	"We should probably check the inn, it has a bar so someone must have seen him."
	"See, you're learning already!"

Heading over towards the inn, the two travellers already felt the hive of scum and villainy wash over them.  Murky sailors blending in with swindlers and honest dockworkers.  The bartender was a species James had somewhat seen on TV before, resembling a green bean-shaped man with bifocals and a moustache.  Koopin and FG walked up to the bar and sat down, the raptor asking:
	"Afternoon."
	"What'll ya have?" said the barkeep.
	"Uhhhh well we just arrived what do you recommend?"
	"Mmmmmm well somethin' from my own homeland'll fix ya right up, how about some Chuckola Cola?"
	"...sure, two pints of Chuckola.  Say, you ever hear of a guy called Kuribo?"
The bartender paused in mid-pour of his service, filling up a glass of reddish-brown liquid before handing it to James.
	"I might...you boys come from the Master?"
	"Yes!" said Koopin.  "Yes we did!  You know where he is?!"
	"I do, mister Kuribo said he was waitin' fer you.  Didn't expect two of ya to come though."
	"Oh we're just travelling together, I'm the one who has to meet him."
	"Alright...I'll let 'im know you stopped by and we can arrange a time fer you to meet.  How long you here for?"
	"Uhhh about two weeks?  Week and a half really."
	"No problem then, I'll let 'im know.  Why don't you boys drink up an' explore the town a li'l bit more, maybe even go see the sights out on the road?  Petalburg's nice this time o' year."
	"Petalburg?  ...that's a great idea, thanks sir!"
The two took their drinks and firmly drank it down.  To James, it was like a strange blend between the most fizzy rejuvenating sugary cola, and the most sweetened grape wine.  It was rather intoxicating, and James could easily sniff out various unusual ingredients which he relayed to Koopin.
	"Fruits...syrup...soda bubbles...huh."
	"What?"
	"...there's no...alcohol in this, like, not the usual kind."
	"Well yeah, but it's just as fun to drink.  Mmmmmph, that's some funny stuff!"
	"Funny?"
	"Yeah, the way they brew this is that you have to tell jokes to the fruit until they laugh, then they release soda bubbles into the brew.  The funnier the jokes, the better the drink!"
	"......this place gets weirder every week, I swear."
	"Hhhehehehee!"
	"Then again, breweries have some weird-ass rituals anyway."
The two drank up the rest, the raptor rather enjoying the strange sweet drink and remembering it for the future.  Koopin also decided to enlighten him about a few facts of the Beanbean Kingdom, the origin of both the bartender and the Chuckola Cola, before they decided to depart.  Directed towards the east side of town, they soon found a pipe just like the one back in Toad Town.

The underground however was far more interesting.  Whereas Toad Town's pipeways were literally just a sewer way, Rogueport's pipeways were an ancient city combined with a sewer way.  Crumbled marble windows and doorways, rusted iron fences that stayed surprisingly well-maintained, as well as one central town square mirroring the one above.  A resplendent fountain stood without water in the middle of the plaza, surrounded by ruined homes and subterranean dwellers of various species.
	"Hooooly..." gasped James.
	"Yep," said Koopin, "this is the old Rogueport...now the sewers.  If you can't handle life above or you're on the run...you can always live out down here.  Only problem is you gotta be able to look out for yourself, guys are a lot more willing to fight ya down here."
	"I'm just kinda amazed, when you said Rogueport was built over a city, I didn't think the city itself was still UNDER it and standing...some of it."
	"Mmhmm!  There's some shops, some houses, the Thousand-Year Door itself but that's kept well-sealed forever now, and the Pit of 100 Trials."
	"...pit of a hundred trials?"
	"Yeah but it's real dangerous, a hundred floors going deeper and deeper down into the abyss with each new floor giving a whole new challenge in the form of some dreaded monsters.  Legend has it that a vile demon unheard of in history resides at the very bottom...very few have ever seen it and lived."
	"...well that's creepy, okay what's next?!"
	"Well we gotta find the way to Petalburg through here, come on!"
Various passageways and interactions with both friendly and non-friendly locals soon lead them towards the right pipe to Petalburg.  The grey crumbling stone halls and constant sewer flow kept James on edge constantly, never liking how narrow the sewerways could get in some areas.  Koopin however took it all in stride, the two fighting back any subterranean thug that tried to come near them, mostly that of the coal-skinned Gloombas.
With a new world before them, they hopped into the green pipe nestled away in some far corner of the Rogueport sewers.  The telltalle PRUN-PRUN-PRUN resonated in their ears, as they left behind the murky ragged surroundings of the port town itself.

Arriving above ground, the first thing James saw was an expansive pure green field of flowers and patches of tall grass.  Hills rolled beneath a pure blue sky, unblemished with the softest carpet green, the only unsightly thing being a dark towering castle far off in the distance to the northeast.  But directly in front of James to the east however, was a clear road towards a small village.  He was reminded of the first time he arrived in the Mushroom Kingdom, the same sweeping air of child-like innocence coming to him once again.
	"Welcome to Petal Meadows!" said Koopin happily.  "Here lie three important areas amongst this beautiful field, an outlying region of the surrounding area of Rogueport, and the most easily accessible.  Firstly, there is Petalburg to the east, a happy little village famous for its flower displays.  Then beyond that is the mysterious Shhwonk Fortress, inhabited by a plague of fuzzies and having a strange connection that castle."
	"And what is that castle exactly?" asked James.
	"That is Hooktail Castle.  A terrible dragon used to live there, terrorising the locals until the legendary Mario came and whupped her butt!"
	"...right, a dragon."
	"Mmhmm!"
	"Big...fire-breathing...dragon.  So the plumber's a knight now?  What, did he use a plunger instead of a sword?"
	"Are you being sarcastic?"
	"Wwwoooow Koopin, you're sharp on the ball today arentcha, hahahahaha."
Koopin rolled his eyes and smirked, taking James along the path as he decided to give him a small tour.
	"Petal Meadows is a pretty relaxing place, especially nowadays.  Not many enemies really to be found around here, especially with Hooktail now gone.  Why don't we visit Petalburg for a bit?"
	"Sure...why does that place sound familiar though?"
	"Maybe cuz it's where my dad is from?"
	"Oh yeah!"
	"So yeah, there's not much here other than being a nice relaxing place...though it IS the only place you can find horsetails."
	"Horsetails?"
	"Yep!  A type of plant that you can make a REAL good salad out of.  I better collect some while I got the chance, it's been ages since I made some nice koopa pilaf.  Very healthy too, they help a lot in curing poisons."
	"Huh, nice, good to know!"

The lay of the land was simple, and as Koopin had said, very few of the locals were hostile in passing other than one or two punkish koopas or goombas, Rogueport locals looking for an easy steal.  They generally stood down at FG's aggressive front, his forceful provocations always keeping them back.  Despite Koopin's displeasure in seeing James get his anger up, he started to understand with passing that it was all just a front.  At least this time.
Soon they reached the delightful hamlet of Petalburg.  It was a charming little village, with red-roofed houses and creamy walls that gave a warmth to the flower-filled humble homes.  A general store and an inn as indicated by the bed upon its sign.  Koopin warned FG that unlike in the Mushroom Kingdom proper, the areas of Rogueport and its surroundings would charge him for staying unless he had a coupon, mainly because the continent was not within the boundaries of the Mushroom Kingdom's legislature.
For the most part James met various koopas and toads, though he did get into quite a discussion with an old white bob-omb who wore a furry-looking hat not unlike that of the Bumpties from Shiver City.  Likewise the bob-omb also mentioned he was from the far north, moving to Petalburg for a change of scenery.  There were also strange plant-like creatures known as Bub-Ulbs, shaped unsurprisingly like bulbs who helped with the care and growth of the local flowers.
Eventually Koopin decided to check in on an old friend, heading up towards a higher-set house at the other end of the village.  Inside was an old green-skinned koopa with absurdly bushy eyebrows, the size of pillows upon his head.  He was somewhat napping in a chair, his home rather small and humble with a bookshelf in front of the door and a fireplace to their left, his chair between both.
	"Um, mayor?" asked Koopin softly.
	"Hnnn-huh?"
	"Mayor?"
	"Ehhhhhh nammuch murphy..."
	"MAYOR KROOP!"
	"Huh?"
The old koopa raised his head, but it was hard to tell whether his eyes were open or not until he looked towards the visitors with acknowledgement, before leaping out of his chair in a panic.
	"WHUH, thieves!"
	"No no no we're not thieves!"
	"Ahhhh knew ye'd be back fer more!  Yer not takin' anythin' THIS time sonny boys!  You can take whut you want, but dontcha dare take my pictures of me an' the missus or else!  I knocked one of ya down, I can do it again!"
	"Mayor it's me, Koopin!"
	"...Rupin?"
	"Shelldon's son?!  Mr. Kennidon?!"
	"...Kennidon...ohhhhh yeeeees, the Kennidon's girl, Rupin!"
	"Um...hhhhh yes mayor, it's me...Rupin."

James smirked and stifled a giggle, receiving a glare from Koopin as Mayor Kroop came closer, grabbing a cane of solid wood and walking slowly.
	"Bin a loooong lon' time since I seen you li'l Rupee!  How's yer ol' dad doin' these days hmmm?"
	"He's great thanks," said Koopin loudly, "I was just in the area and thought I'd say hello!"
	"Well arentcha a sweet li'l thing?  Ya wan' some candy?"
	"No thanks!"
	"Iiii remember ya used to love mah lemon candies, always' smilin' up at me an' askin' why my eyebrows were so huge.  An' I'd say that the missus had the finest comb in all the land!"
	"Yeah I remember that well!  Um, are things okay here?!"
	"Shelldon must be real busy to not even see his own parents nowadays!" said Mayor Kroop.  "But they'd sure be proud of their son, an' you li'l Rupin!"
	"Um, mayor?!  My grandparents haven't been here for five years!  Remember?!"
	"Ohhhh...huh, how time flies fer all of us don' it?!  Now who's this strappin' lady right here?!"
	"L-lady?!" cried out James.
	"This is James!" said Koopin loudly.
	"Jane?!" misheard Kroop.
	"Yeah!  James!  We're together!"
	"Ohhhhh how lovely!  Yanno I always thought you'd settle down wi' a nice girl Rupin.  She better be takin' care of you too!"
	"Oh SHE is alright!"
Koopin's turn to smirk, looking up at FG who grimaced back at him before Koopin asked:
	"Is everything okay here mayor Kroop?!  You were panicking a li'l back there about thieves!"
	"Ohhhh dontcha worry none about it Rupee, jus' usual trouble, nuthin' you worry yer li'l head about."
	"Are you having a problem with thieves in the area?!"
	"Well...I don' wanna be an ol' bother anymore than I already am bu' sum damn uppity boys tried to come into my house an' ransack me two days back!"
	"REALLY!?  That's awful, who would do such a thing?!"
	"I dunno, what is this world comin' to these days!?  But I'm sure they'll be caught soon, they only took my ol' purse, I can always get more money, all it had wuz a dizzy dial an' about fifty coins!  Long as they don' take my pictures...my memories....they're the only thing I got left hangin' on in my ol' head."

A sombre air weighed down upon him briefly.  James glanced at the photos behind his chair, showing him in his younger days with a beautiful female koopa.  He smiled softly before asking in the same louder tone as Koopin:
	"What did these thieves look like?!"
	"Ehhh, wassat?!"
	"What did these thieves look like?!  That way I can uh...report them to authorities if I ever see them!"
	"OH uh...wuz kinda hard to tell, all I saw wuz that there were four of 'em, an' they were all uh...different colours!  Can't quite tell whut is whut though, I only remember green an' red...and uh...orange?  I swear on my cane there wuz four of 'em though, one of 'em came close to my pictures an' I smacked him right on the beak!  Gave it a good crackin'!"
	"HAH, nice one sir!  Alright then!"
	"We uh better get going now!" said Koopin.  "It's real good to see you again mayor!"
	"And you my li'l Rupee!" said old Kroop.  "You jus' mind yer manners an' I'll give you sum ol' lemon candies again next time!  Tell yer dad I said hi now!"
	"Bye sir!"
The two left the old mayor's home, walking back down the steps of the house onto the main pathway of the village.  Koopin already saw the look in James' eyes as he began scanning the area.
	"You're gonna go find these thieves aren't you?"
	"Yyyyyyyep."
	"Oy...James, let the authorities handle it-"
	"No.  I think I know who these guys are anyway."
	"Wait, really?!"
	"Yeah.  Hold up a sec."
He headed towards the gate that lead towards the Shhwonk Fortress and asked the koopa guard.  Sadly he was not helpful, saying that he had seen some shadows around the mayor's house, but he couldn't catch the thieves or see what they were.  However, the old white bob-omb was nearby, and spoke up with a thick slavic-sounding accent.
	"I see them."
	"Really?" asked James.
	"Da.  They crept through night, like oafs.  They head past guard, skirt round and over gate when he went to check on mayor.  I was in house here, see them creep past."
	"Did you get a good look at them?"
	"Da.  Four koopas, red, green, black, yellow.  Hehehe...my eyes good at night, spent years at sea in navy, spotting ships at night."
	"Wow...that's really helpful, thank you!"
	"No problem.  I do not like thieves.  They cripple a populace as bad as traitors."
	"Right...so uh, mind if we get past here?" asked James to the guard.
	"Um...you should really get the mayor's permission first before you can."
	"So I should go back there, talk to the mayor again to explain that the thieves are running away RIGHT NOW towards that fortress, with HIS coin purse, and I have to wait a few more minutes just to make everything squared away by wasting everyone's time?"
	"...well...I...fair enough."
The koopa looked rather shameful before opening up the gate and allowing both James and Koopin to pass through with their thanks.  Heading out of the humble village of Petalburg, James could already see the fortress up ahead.  It was strange how the last time had met these certain thieves, he had also been heading towards a fortress back a year ago, chuckling to himself.