I have to say that Aisha's voice actor does a really good job.
By the way, it seems that skull-mark enemies don't have the ability to raise the alarm, so you can get as close as you want as long as you don't actually make contact.
And it seems that you have 4 general routes:
>Find a small boat and escape by yourself;
This requires you to find the small boat in the pirate ship's attic (or make one yourself with 5 pieces of lumber and the Talented trait),
Figure out a way to deal with the Kraken,
Find a map of the surroundings and at least 3 navigational equipment,
Have 3 food items and 3 drink items.
>Clean up and hijack the pirate ship;
This requires you to take out all pirates in the pirate ship,
Figure out a way to deal with the Kraken,
Recruit 3 sailors,
Have 6 food items and 6 drink items.
>Cooperate with the pirates;
This requires you to figure out a way to deal with the Kraken,
Kill the pirate leader,
Break all 3 Illithid statues around the island.
>Escape using a barrel.
This requires you to examine the barrel in the pirate ship,
Have 3 food items and 3 drink items,
And have 8 or more Luck (even with the Lucky trait, this is a tall order).
First order of business is opening up access to places: you want the Diving Swimsuit, the Rope, the Crossbow and the Waterbreathing Salve.
For the Diving Swimsuit, you want to get a sewing kit from the B2F prison (where the other girls are at); get intel from the old man in the Rest Area (B2F north exit) and examine one of the trash bags in B2F southeastish area for sea serpent skin; get the torn swimsuit from B3F northwest hut.
For the Rope, you get it from B2F south area; you need 1x lumber and carpentry tools from B2F northwest OR the Diving Swimsuit.
For the Crossbow, you get it from the weapon storage accessed from B2F northwest, but it's too big and heavy for Aisha to pull by hand so she needs a crank from pirate ship B2F warehouse (SE-most door). You can move the golden statues.
For the Waterbreathing Salve, you need to loot the pirate ship (B1, SW door) for a key, and get it from the captain's room (1F, N door).
With rope, you can enter the pirate ship from beyond the smithy room.
With rope and swimsuit, you can access cave B2F SW underwater area for a rusty chain.
With rusty chain and 1 oil, you can reactivate the cave B3F NW gondola to access a new area where you can loot a bunch of stuff and the 1-feet pole. If you have the medal from pirate ship B2F warehouse (the one that triggers a timed event into a dice-roll event) you can unlock yet another new area with an Illithid statue. Break it with a hammer from the smithy room.
With the 1-feet pole, you can access the cave B3F SE hidden chamber for more loot and essential items.
With rope and crossbow, you can hookshot over past the weapon storage area for another Illithid statue.
With the pirate ship key, you can open up the attic door for a small boat and the last Illithid statue.
After breaking 2+ statues you can talk to one guy in the pirate ship B1F, and open up the shop in the pirate ship B1F south exit.
With swimsuit (and probably waterbreathing salve) you can access the Underworld area beyond the waterfall in cave B2F west exit. Lots of skull-mark enemies here.
There's more stuff but I'm too tired to write more.
