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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.