Sort:  
  • Boat (fish from boat, entertain, explore, access different parts of the island easier)
  • Tent (habitation is an immediate need)
  • Matchbox (Heat and cooking food, boiling water)
  • First aid kit (health is important)

If it was a flashlight with unlimited batteries now we're talking. Or unlimited toilet paper that would be big. A mirror doesn't light the fire on cloudy days. Insect repellent and sunscreen are very interesting if never ending supply as well as how many flares for flare gun?

Honestly i may be willing to trade First aid kit for fishing pole... but i'd need to know how much line and how many fishing hooks. Also depends on how many matches in the match box.

What's nice about the boat and tent is a quantity of one is sufficient.

Hmm, I think an axe is important. If you have an axe, you can build a shelter, and repair stuff. The tent will be soon or later gone after a strong storm, but with the axe you can build smth. new.

you can build a habitation but i doubt anything good enough to protect from insects or rodents AND you need something right away. Axe is a great one. And maybe i'd consider it over first aid kit. You can't live in fear of something breaking... the axe can break.

Compass for direction
Hiking boots to navigate around
Flare gun to signal rescuer
Knife for weapon/food prep (lighter than axe lol)

this is tough

I agree on hiking boots,
I would add the axe (more versatile than a knive for e.g. creating shelter),
the rope (also versatile for storing food in a tree, for construction of tools, etc.) and the first aid kit (for obvious reasons).

Okay, you changed my mind about the Axe (agree to that) 😅

And yeah, I remember the importance of rope... best way to store (or safeguard) food is to tie it up between 2 trees.

You can´t be sure. I would no rely on hopes :)

Walking barefoot on an island that you don't know is risky. Cut your feet badly and you won't be able to walk properly anymore. It will slow you down.

So it seems you will pick a Knife as one of your items.

How about the other 3 items that you will choose?

Boots are a good choice.

What will you do with the Kayak? do you know where to go?

Fishing pole feels like a waste of choice; it wasn't mentioned that there are fish within the island/around near the island.

There is a huge difference between a knive selfmade out of stone and a metal knive.

An island so large that it takes let´s say 4 hours to walk across. Jungle vegetation, small river, sand beach :)

Not sure, but without a knive or axe you won´t create easily a shelter.
Your survival chances on a boat without navigation and loads of food and water are zero!