Question

I need help on number 2

Answer 1

I have an idea, the river is Hudson. The Dutch settlement was built along the west Hudson and was called New Amsterdam. Also before 1665, New York was called New Amsterdam before the Dutch surrendered to the English.

Answer 2

I think the person that's being described is Henry Hudson. He took several trips out to sea and successfully made it to the New World on his third one. I think New York was also called New Amsterdam under the Dutch, but I'm not certain.