
DM Amazing Red |

Bjorkus, Chubs strike their targets while Opal has no such luck as the invisible stalker proves too quick and dodges her rays of lightning. Kal defiantly fires at Harrigan, but all three shots inexplicably miss. Barnabis Harrigan smirks as he watches the arrows sail past him, only one coming even close.
The stalker retaliates against the goblin captain.
1d20 + 12 ⇒ (15) + 12 = 27
2d6 + 4 ⇒ (1, 2) + 4 = 7
1d20 + 12 ⇒ (14) + 12 = 26
PCs up.

Bjorkus |

Bjorkus manuevers into a flank with the captain and delivers his bovine wrath.
Raging Power Attack: 1d20 + 15 + 2 ⇒ (6) + 15 + 2 = 23
Damage: 1d8 + 23 ⇒ (5) + 23 = 28
Iterative: 1d20 + 10 + 2 ⇒ (19) + 10 + 2 = 31
Damage: 1d8 + 23 ⇒ (1) + 23 = 24
Horns: 1d20 + 9 + 2 ⇒ (11) + 9 + 2 = 22
Damage: 1d6 + 7 ⇒ (6) + 7 = 13

DM Amazing Red |

And Bjorkus pummels the stalker until it dissipates.
Reflex: 1d20 + 7 ⇒ (15) + 7 = 22
Peppery dodges the lightning and casts a spell of her own.
1d20 + 8 ⇒ (12) + 8 = 20
And the whirlpool is now gone!
It is the final leg of the race, the Storm and the Wormwood are still neck and neck.
I need 4 profession(sailor checks) from the Storm please.

DM Feral |

Opal Assist: 1d20 + 6 ⇒ (1) + 6 = 7
Opal Assist: 1d20 + 6 ⇒ (3) + 6 = 9
Opal Assist: 1d20 + 6 ⇒ (18) + 6 = 24
Opal Assist: 1d20 + 6 ⇒ (7) + 6 = 13
Chub's Sailor: 1d20 + 15 + 2 ⇒ (8) + 15 + 2 = 25
Chub's Sailor: 1d20 + 15 + 2 ⇒ (12) + 15 + 2 = 29
Chub's Sailor: 1d20 + 15 + 4 ⇒ (7) + 15 + 4 = 26
Chub's Sailor: 1d20 + 15 + 4 ⇒ (17) + 15 + 4 = 36

DM Amazing Red |

Well, the Wormwood is a lot faster and Harrigan is better at captaining than Luthor is.
And the Storm adds another 1 to their score.
The Storm leads the Wormwood by a considerable margin. Harrigan makes a determined effort to catch up, but he clearly has no chance of winning.
You are victorious, crossing the finish line as the clear winners.
As winners of the Free Captains’ Regatta, you receive the regatta’s rich prize purse—with 16 entrants, including themselves, the purse totals 8,000 gp. More importantly, the PCs gain a seat on the Pirate Council of the Shackles. The Master of the Gales ceremonially attaches a broken, silver-plated manacle on Chubs' wrists as a symbol of this honor, representing the your freedom from the constraints of other nations’ laws and authority, but also the responsibility that now binds them to the welfare of the Shackles and its people, whom you now represent. Finally, the Master of the Gales presents the you with a deed granting you lordship over a small island in the north of the Shackles. But a deed is only a piece of paper; in order to truly claim dominion over this island, you must explore it and deal with any monsters or other inhabitants there.
You also get 2 disrepute and infamy for winning the race as well as Harrigan's undying hatred if you did not already have it.

Bjorkus |

Bjorkus whoops and cheers as the Storm crosses the finish line by a healthy margin and the bull literally hurls Chubwart and Opal into the air with glee (catching them when they descend).
”Did you see the fury on Harrigan’s face?” Bjorkus says excitedly. ”It should be obvious who’s the better crew now.”

Bjorkus |

Realizing Luthor was, in fact, too big to toss, Bjorkus settled for a tight bullhug.
”You did great Luthor”, the minotaur rumbled. ”The Sanbalot’s mostly in one piece and the crew’s alive. That’s better than most can claim.”

Bjorkus |

The minotaur raises an eyebrow at Luthor and Kal’s somber tones.
”You two are terrible pirates, you know that? You should be excited! We ousted Harrigan and won the regatta. We’re gunna be f**%ing legends! Nobody goes from pressganged galley-slave to Free-Captain and Pirate Lord like we just did.”

Bjorkus |

"I'd say we're all due a bit of time to celebrate and rub our win in Harrigan's face. Kal has the right idea even if he is a furless whelp", the minotaur says with a laugh.

DM Feral |

Arriving back in Port Peril the crew is greeted with boisterous cheers and standing applause. It seems every pirate, from the lowliest swab to fellow Free Captains, make an effort to congratulate the party on their win and talk about the race. Even some of the more 'competitive' participants stop by to buy the winners a round of drinks - minus Harrigan.

DM Feral |

A few days, hundreds of drinks, and several drunken romps later, the crew's had their fill of celebration and starts to pressure the captains and officers to visit their prize.
The party and crew arrive on the docks to find the ancient Master of Gales awaiting them. The old man seems to read the party's intent like it was written on their faces.
“It’s called the Island of Empty Eyes,” the Master of the Gales explains, “for the queer statues that leer over its shores. Uninhabited and fraught with danger, make no doubt, but naught that pirates of your capabilities can’t handle. You’ve landed a seat on the Pirate Council as well, but winning a race don’t make a sailor a captain, nor a freebooter a lord. You’ll need to show the Council you can tame the island and make it your own, if you want to claim your seat. The lords of the Council will come calling in three months to see if you’re worth the honor that’s been bestowed upon you, and they’ll expect to be feted as befits pirate lords of their stature. Provided you look like you know what you’re doing, they’ll take your oath of loyalty and grant you your seat on the Council. If not... well, you wouldn’t be the first winner of the Regatta who failed to live up to expectations.”

DM Feral |

The old man shakes his head.
"Perhaps, but if I told you anything I'd be ruining the purpose of this challenge. You've got to learn about this place on your own, by your own wits, and by your own skills. All of the pirate lords are forbidden from lending aid", the aged pirate explains.
"That includes Tessa, even if your bull is riding her every chance he gets."

DM Feral |

Two uneventful weeks later, the Raging Storm, the Sanbalot, and their crews arrive at the aptly named Island of Empty Eyes. It's a small overgrown jungle island (no more than 10 miles across at any point) but with a little work, it could be home. All around the island's perimeter, massive weathered statues of single-eyed humanoids stand guard against the sea.
From which direction do you want to approach?