You meet a woman whose son admires you and would like to sail with you. She thinks he deserves his own ship though, and asks you to help him get one.
First you will have to talk to the son, who's in the family's house right behind Josette Mercado (a separate instance which becomes available once you accept this mission).
After this, the main part takes place in Pensacola and requires you to board a merchant ship (around level 17). It will be guarded by two slightly lower-level escorts (about level 12-13). Once you have done that, return to St. Rose's Bay and claim the reward and the follow-up mission from the son.
- Board the French Merchantman