What of the island is small? Why you need direction for?
Hiking boots? I think I'll be barefoot mostly.
Flare gun for rescue? With abundances on the Island I doubt you want to be reached. That's just me.
Knife, I am sure you can make one there.
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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.
Your right. Could be worms in the sand that bury I to your feet, lay eggs and have worms crawling out your skin later.
So it seems you will pick a Knife as one of your items.
How about the other 3 items that you will choose?
On the contrary, boots might be one of them, but I want the kayak moat of all for fishing, thus a fishing pole would be my next choice. Why bother with a tent if there is vegetation enough and wood to build my own? Ever feel island storm winds? A tent will be ripped to shreds.
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.
The island is a mystery. But i rather take my chances out at the open ocean if the island is jack shit. Otherwise, cool I got a boat to travel around the island. And boats are cool man. Lol
There is a huge difference between a knive selfmade out of stone and a metal knive.