Ireena responds, "Colorful wagons are almost always the Vistani..."

The sounds stop as you approach. A voice emerges from inside. "Hello?"

Hello, my name is Garrick. May I ask with whom I am speaking?
Garrick tries to see what is in the wagon.
Perception 20

Peering through a tinted window, you can see various letters and packages. "I'm Barovia's mailwoman, Zondra Zalken, but you can call me 'Z'."

Garrick looks to see if the duo recognizes her and their reaction to it.
What seems to be the problem here? Why have you stopped in the crossroad? He specifically is looking for deception.
Insight 12

"I'm just sorting through mail before my next stop. I want to be prepared when I arrive."

You hear no deception.

"Mail? What kind of mail do people get around here?" Kessintra wonders aloud. Meanwhile she will study the wagon more closely, wondering if it might be able to carry all or at least some of them.

Investigation 22

"And where is your next stop? This land seems rather barren."

Persuasion if needed to get an answer: 10 -.-

The wagon is sizable, being able to hold quite a few letters. You can estimate about 500 letters fitting inside.

"I get all kinds of mail to deliver. Love letters, memos, invitations, requests. I try not to peek too much. As for my next stop, that would be the village of Barovia." Ismirk furrows his eyebrows. "Since when do letters get delivered here?" "Since a few days ago. This is my first trip this far away from home, however."

"Interesting...And Strahd doesn't mind you doing this? It might bring some joy to people, after all, and that seems all but outlawed here."

"Strahd hasn't bothered me yet. If he does, I'll do my best to deal with it. I've actually delivered a letter for him myself. Perhaps he has a use for my services."

Kessintra pauses, strumming idle notes on her lyre as she thinks. "What if...someone wanted to mail a larger than usual package? A rush delivery, as well."

The question stumps her for a moment. "Umm..... I suppose I could put the rest on hold. Why?"

Kessintra gives a slight smirk, looking around at the others and speaking more softly so Z can't hear as they discuss. "This could give Ireena some extra protection on the way to Villaki. She goes in the cart and we guard it from nearby, pretending to be traveling separately."

Ismirk shakes his head and whispers back, "We shouldn't send her in alone. Both of us should go in, at the very least."

The drow nods. "True, then you can do something if Z tries anything funny. Meanwhile, Kessintra will be out of view, sneaking around as rogues do, while the party escorts 'Ireena'. But...hm, it may become obvious it's a trick if we don't have an Ismirk with his sister..."

"If there's a need for an Ismirck lookalike," says Chipper, "I have a spell I could use. Won't help with physical inspections, but should be enough to fool any casual glances."

[[
If Kessintra is planning to disguise as Ireena again, Chipper could disguise self as Ismirck.

Also, made sure to mark of a spell slot for Mage Armor
]]

((Does the wagon have windows/could one shoot ranged attacks/spells out of it?))

It has a few windows that can open if you wanted to make range attacks. They also provide line of sight.

Zantorin listens to the plan as it comes together, watching the faces of both Ireema and Ismirck to see if I can get a read on them about it. maybe it's just me, but I'm not too crazy about this. As long as you two are good with it then ok. I prefer not to stay too far back though. 

He looks to Z, addressing her through the window, who would you be delivering to in Barovia?

Kessintra tilts her head as she studies the wagon, clearly in her element as she schemes and plots. "Hm...Perhaps two tricks in one? Real Ireena and fake Ismirk go inside?"

Ireena has an enthusiastic smile on, but Ismirk seems a bit anxious about the idea. 

Z responds, "Just a few people. Nobody I can recognize the name of. I'm sure they can wait."