I, Your Father, Carry a Big Stick

This is the Crew we came up with on Discord. As for Harem-related stuff, the MC would have a personality very similar to Drake's. He might have a casual fling every now and then, but he wouldn't be picking up stray girls and adding them to his crew. Most of his crew will remain the Servants he has summoned.

Roles Captain: Francis Drake(f)

First Mate: Musashi(f)

Second Mate: Chiron(m)

Boatswain: MC(m)

Cook: Benienma(f/head pats only)

Doctor: Asclepius(m)

Navigator: Astolfo(?)

Shipwright: Caenis(f)

Sniper: Atalanta(f)

Ship: Golden Hind