What kind of boat would you get IF you wanted to explore the high seas?

Let’s say that you could spend no more than about 100K. Specifically:

a. How big would it need to be (I’m thinking about forty to fifty feet long).

b. Would you want a sail boat (with outboard motors), or a cabin cruiser, or something else entirely.

c. Let’s say I wanted to live on it in Oahu, how much money would I be looking at to “park” it in port on average.

What else would I need to know that is not commonly anticipated. My only experience is in the Navy stationed primarily on a minesweeper.

Thanks,