Melanthios blinks at this rather abrupt dismissal, then shrugs.

"I always find it’s best to explore the taverns first.  What say you all?"

"it does seem that is often where information is kept."

Koris looks back along their route to the harbor master’s. “Are you sure the harbor master’s isn’t the place to start? A wilderness guide sounds like what we need. Someone who’s familiar with the island, and experienced enough to lead us.”

Melanthios snorts.  "And you think they’ll be at the harbor master’s?  Any guide worth their salt will be in a tavern."

“I mean, the sign said they had contact information...” Koris looks a little confused.

She's very powerful. Mustn't forget that. Poole is wandering about in a circle, clearly feeling the pull of all the stimuli a new city presents. After Melanthios and Lorahana speak, she talks again to herself quietly: makes sense to want a drink on a day like today.

She moves closer to the group, and you can see she's fairly well-armed. There's a rapier at her belt, and a shortsword in a scabbard on her back, and at least one dagger hilt pokes out from a boot, maybe another under her studded leather armor with very close looks. She's got a small pack.

"This city smells amazing. I'd like to explore just a bit on the way to the tavern, if that's okay with you all. And that bulletin board of guides would be good to scan before we try the tavern. We don't want to perish like the last group, so local expertise and something more than rumors about the Soulmonger are top of my list."

While the six adventurers attempt to absorb their new surroundings and develop a plan for the day, a very round male lightfoot halfling saunters up to the group. Wiping the sweat from his brow with an orange handkerchief, he jovially interrupts the group's dialogue. "The sun shines upon us in more than one way today, friends! A boon for us both that we have crossed paths! I am Gondolo..."--he offers a perfectly executed bow as he introduces himself--"...and you are, most unmistakably, in need of a guide. Someone who's ventured into the jungles of Chult and can expedite your expedition. My partner Faroul and I are just the ones to do so. For no other guides have a triceratops at their disposal!"

Gondolo smiles warmly, takes a deep breath, and wipes his brow a second time. "No need to say a word. No need at all. Think it over as you enjoy Port Nyanzaru today. Ask for me or my partner at the Thundering Lizard..."--he points southward as he says this--"...near the red bazaar. We'll talk over a pint or two of nej and make the necessary arrangements."

The flaccid halfling bows a second time and turns to walk away. 

Melanthios blinks rapidly, then looks at the rest of the party.

"Anyone else think that was a little too convenient?  And what in the Nine Hells is a triceratops?"

Would Poole have noticed what Gondolo was doing as the party was guided through the streets to this place? How he discovered them, what he was doing beforehand?

Passive perception is 17 but I'm happy to roll if you need a check...

 Anzir shrugs. "I'm sure we look like a bunch of easy marks. But...I'm curious to see what this triceratops is as well," he says. "Besides, he told us exactly where to get a drink, so he's already a leg up on any other guides."

The dragonborn, enjoying the warmth on his bare skin, heads to the red bazaar.

Quote from rkmobius >>

Would Poole have noticed what Gondolo was doing as the party was guided through the streets to this place? How he discovered them, what he was doing beforehand?

Passive perception is 17 but I'm happy to roll if you need a check...

 Gondolo approached the party from the west; so, it's a safe bet that he came across the bridge to the west of the Wakanga's villa. 

Irma sizes Gondolo up and says, "You look like the best guide to point someone to a better guide. Why don't you tells us about some of your competition, possibly someone who's actually been to the jungle in the recent months."

Quote from Jack_Joke >>

 Gondolo approached the party from the west; so, it's a safe bet that he came across the bridge to the west of the Wakanga's villa. 

 (But he hadn't been, like, coordinating with another sketchy person, beforehand? Seems largely honestly intended?)

Poole nods at Anzir, then fades into the city, completely comfortable amid the hubbub. She does not range too far from the path to the red bazaar, just a few blocks away, and finds 2-3 people in the market who seem talkative, asking about: Gondolo and his triceratops; O'tamu's reputation; news about a previous party who arrived and departed the port recently geared up for an expedition for an undead relic and didn't return; who's really a good guide and knows what they're doing. She aims for bored-but-observant-looking market stall operators, that kind of thing, and she's looking to avoid the sort of people who make their business preying upon naive new arrivals, having seen that particular play on repeat in Baldur's Gate.

Some rolls if needed:

 Annnnnd somehow I've boofed this up, so feel free to ignore me! I copied and pasted code minus a front bracket and now the post seems irrevokably broken. Sorry all.

Poole sadwalks (in- and out-of-character) directly to the tavern indicated by Gondolo, orders a drink, and tries to forget about her adventure in the marketplace

Quote from Winenose >>

Irma sizes Gondolo up and says, "You look like the best guide to point someone to a better guide. Why don't you tells us about some of your competition, possibly someone who's actually been to the jungle in the recent months."

Gondolo pauses ever so briefly, caught slightly off guard by Irma's remark. He then lets out a chuckle. "Ha ha. Excellent. Testing my mettle. Making certain I'm more than an empty boast. Excellent. You're a clever one, but I won't be doing your legwork for you. Not at all. No, Not at all. You'll find postings for the legitimate guides at the inns, taverns, and harbormaster's."

His emphasis on the word legitimate suggests to Irma that other types of guides might be operating in Port Nyanzaru.

Quote from rkmobius >>

 

Poole nods at Anzir, then fades into the city, completely comfortable amid the hubbub. She does not range too far from the path to the red bazaar, just a few blocks away, and finds 2-3 people in the market who seem talkative, asking about: Gondolo and his triceratops; O'tamu's reputation; news about a previous party who arrived and departed the port recently geared up for an expedition for an undead relic and didn't return; who's really a good guide and knows what they're doing. She aims for bored-but-observant-looking market stall operators, that kind of thing, and she's looking to avoid the sort of people who make their business preying upon naive new arrivals, having seen that particular play on repeat in Baldur's Gate.

Anzir and Poole (and whoever else joins) reach the Red Bazaar within a few minutes. A host of vendors line the street and narrow walkways, offering locally produced meat, vegetables, tropical fruit, tej, light tropical clothing, insect repellent, rain catchers, and other household goods. The buyers and sellers in the Red Bazaar are predominantly locals.

Poole finds the task of conversation with the Chultans to be relatively easy, making conversation here and there and casually asking questions, questions that the locals have undoubtedly been asked many times before by visitors from the north. Within thirty minutes, the adventurers who visit the Red Bazaar have picked up the following information:

• Gondolo and his partner Faroul do indeed own a triceratops; they originally purchased it with the hope of entering into the dinosaur races that happen each week, but the beast proved to be too old and slow. So, now they utilize it as a highly effective pack animal for expeditions into Chult's interior. 
• Wakanga O'tamu is one of the seven merchant princes who collectively rule Port Nyanzaru. All princes are Chultans, and each oversees a particular area of trade. Wakanga deals in knowledge, information, lost lore, potions, and scrolls. He seems generally well-liked, but a few vendors do make a few jests about Wakanda's being easily wrapped around the finger of any intelligent woman. 
• Parties of adventurers leaving Port Nyanzaru for the jungles are somewhat common. Few return in tact; some return with wealth; all return with tales. No specific information about Syndra Silvane's previous expedition is revealed, however. One of the merchants laughs as she chimes in about jungle expeditions, "Watch out for any mist with a blue tinge to it. It spreads a fever that drives people mad." 
• The names of a few guides are offered up in addition to Gondolo and Faroul. "Possibly the druid Qawasha," says a local with a disinterested shrug. "Nay, Azaka Stormfang," chimes in another. 

Quote from rkmobius >>

Poole sadwalks (in- and out-of-character) directly to the tavern indicated by Gondolo, orders a drink, and tries to forget about her adventure in the marketplace

 Very near the Red Bazaar is The Thundering Lizard, the inn mentioned previously by Gondolo. Loud music and rowdy singing erupts from the place's open windows and doors. Anzir and Poole take in the scene, somewhat relieved to be out of the unrelenting sunshine as they sip the local form of mead called nej.

Poole's spirits begin to rise as she lets the rowdy singing wash over her, and the nej begins to do its work. She keeps an eye out for anyone who's keeping an eye out for her. She makes amiable conversation with Anzir while they wait and chat with any locals who come by. "So you seem excited to be along for this ride. Care to say why? You make me feel... underpacked, and yet I suspect we'll need to bring more with us to have a hope of surviving this joyride. Should we take bets somehow on who makes it back alive or... well, that would be in poor taste. We've barely met each other."

Melanthios lounges back in his chair.  He appears to be completely at ease and lazy, but his eyes are tracking everything.

"Could be good in theory, but if you bet on yourself it won't be much help."

Anzir takes a swig of nej and savors it before answering Poole. "I've been on an expedition or two," he says, turning his eye on the squirrelly rogue. He leans in with a steady gaze. "Traps, angry natives, ...undead. I like to be prepared."

Koris sees the others heading for the red bazaar and calls after them. “I’ll be along shortly, I’m just going to make sure we cover our bases.”

Koris heads for the harbor master’s and the boards for explorers.

Irma goes with Koris. "We should not move around alone."