The second one is correct. The first one makes it sound as if he is a 'rich' (not a noun) and a 'sailor,' who is famous for being a sailor.

One article per noun no matter how many adjectives precede it.

On second thought, I suppose you can double up with superlatives, but it sounds stilted and kinda anachronistic.

The greatest and the most wonderful cat.

The second one is correct. The first one makes it sound as if he is a 'rich' (not a noun) and a 'sailor,' who is famous for being a sailor.

I can't think of a situation where you would use the indefinite article (a/an) twice in a single noun phrase. In most cases, you wouldn't use the definite article twice either to describe the same thing.

*The green and the blue marbles

clearly means two separate groups of marbles.

The exception, you can use multiple (definite) articles with superlatives, but it sounds stilted and kinda anachronistic.

Isaac Newton was the greatest and the luckiest of the mortals.

(From the New York Public Library: http://web-static.nypl.org/exhibitions/newton/introduction.html)

These adjectives use the definite article because you must be referring to a definite noun when using them. You can't say a greatest mortal. I would argue that the "the" can be analyzed as a necessary part of the superlative, at least in writing.