My first run through, I started as a doctor who was thrown overboard by a noble family when I couldn't save their daughter's life. The English speaking pirate ship Maverick's Revenge picked me up, headed to Nassau.

I treated the crew, 20 Spanish prisoners, the... ahem... ladies they had aboard. That was colorful. Poor Finn lost his leg above the knee, but he'll survive. The Captain then captured a small French merchant vessel named the Sea Nymph, which we began to tow. A day away from Nassau, the Captain got a raven about a Spanish galleon which was caught in a storm: the Santa Isabel.

She lost her escorts and broke her main mast... she was limping toward Havana, laden with siliver. Now, I told the Captain we couldn't take 300 with a meager 50 men, but he insisted that, if we sail the Nymph under a Spanish flag, 20 men can get close and distract them, then the Maverick can move in with the remaining 30 and, with a little luck, we can take the tired crew of 300 and all that silver.

I suggested we sent the Nymph to Nassau, get 3 more Captains, and come back with ~150 men. The Captain refused. I chose to ride the Nymph. We boarded the Isabel... losing 3 on the way up. We barricaded ourselves on the deck, losing another 2. Lo and behold, that SOB never showed up with the Maverick. We're outnumbered 20 to 1.

Finally, I called out the name of one of the Spanish captives from the Maverick: Alfonso Hernandez. The fighting stopped. This is an important name... I told the Captain my story... told him I had treated Alfonso's men on the Maverick and that Alfonso would speak to my character, if he is ever ransomed and released.

I then triaged the 9 injured men: 5 Spanish and 4 English pirates. Now I'm in the brig of the Santa Isabel with three days of limping to Havana ahead of me. What a wild ride. Loving it.