Party Motivations

Just me spitballing ideas here:
Since, I don't think at least, Naat's character isn't the stealthiest of types, being a stowaway brings up trouble (mostly how'd he sneak on the ship with a glaive). So maybe we do a mix between Shipwrecked and Trade Mission, this way it is easier to meld characters together and it gives to the story more. Ygne and Naat's character could be on the trade mission ship, so Naat's maleness doesn't interfere with the all-female ship rules and Ygne gets the profit story, it also allows Jabes' ship to be on some other business, as imagined.

How we end up together at the island:
The Sea Witch is caught in the storm, just as the Trade Mission ship is, causing the two ships to crash into each other. Gives another reason why there is so few survivors.

Again, just spitballing, I'm just a stowaway so I'm fine either way.

Works for me! Maybe the Sea Witch was even chasing the other ship down when the storm struck, blew them both off course, and smashed 'em together!

That sounds smashing, lads! I'm all for it.

Sounds good to me, HypCo! Clean and simple :)

Looking at their personalities (specifically their love for fighting, being unafraid to spill blood, and especially the recklessness), Frick and Ygne look like they'd get along spectacularly. More than just trade partners, do you wanna be buddies, Naat? :)

Absolutely! It's always nice to start with some sort of connection to at least one member of the party :)

Things are really coming together. It'll be fun to bring in the trade mission because it offers some additional details that I'll share with the players of the PCs on the Trade Ship once that is solidified. So, the Sea Witch was chasing after the Trade Ship (anyone care to name her?) when a once-in-a-lifetime storm struck, smashing both ships into each other. I am going to add in the additional detail that as far as the crew of the Sea Witch is concerned, this island was not on any of their charts.

Currently, the party is starting out like so:

PC's on the Sea Witch: Elspa, Jarveena, Ryte
PC's on the Trade Ship: Ygne, Frick

HypCo, you can switch ships if you like, your call.

Are the crew of the Sea Witch pirates? Maybe it was said, or at least implied, but I wanted to be sure. Elspa would sign up with the crew regardless, applying muscle and ferocity to both the Sea Witch and her opponents.

Going off her background on her player sheet, I'd say they are pirates.

Also this: That was how Leatha found her. Leatha "Fishwife" Gabranth, captain of the all-female crew of the Sea Witch, was the most fearsome corsair of those seas.

While it would be easier for Ryte to be aboard the trade ship, I think I like the stowaway idea more.

HypCo, to expedite the process, you can roll a stealth check vs. the party's passive perception. You can give yourself advantage or disadvantage depending on how you view your plan - for example, if stowing away was a well-planned covert act, give yourself advantage; but, if it was it more of a last-minute desperate act give yourself disadvantage. I'll leave it up to you.

Elspa's passive Perception is 14.

I'll just straight roll. It wasn't well planned but it was premeditated. Ryte knew to get away from the murder, his best bet would be a ship and he wanted to leave a ghost.

That'll beat everyone's passive perception score I'm pretty sure!

Motivations:
Lost in "abandonment" and a foretold downfall, Rygnar makes his way to the island in search of his chain holder. With nothing but his meager belongings, he "persuades" a fisherman to set sail with him. The fisher remains afar from the island and seeing no way to convince Rygnar to not go, gives him his pack and a 'good luck'. Rygnar swims for Rygnar must as he will not see this telling become reality.

Party History:
Elspa found Rygnar on one of her hunting trips and found his size would be a formidable ally and slowly nursed him back to health. Rygnar saw Elspa has his savior and in turn viewed her as a kid-sister, staying close by her wherever she went. Until he saw an opportunity that was beneficial for her and one in which he couldn't follow her.