
Opal Windsong |

know arcana 1d20 + 11 ⇒ (10) + 11 = 21
"Holy hell! Is that creature just randomly living hereabouts or did someone summon it to cause us problems?
If it is within her distance to do so, Opal will toss off a fireball at the creature.
damage 8d6 ⇒ (6, 2, 1, 3, 2, 4, 3, 2) = 23
she will leave the energy type as fire, unless her knowledge roll tells her that something is better to use

DM Amazing Red |

You know that it's a dragon turtle. A full grown specimen is normally huge but this one happens to be a giant version of it. Since you asked, you know it's immune to fire, so you would have to make it a different type.
Since the range on her spell is over 700 feet, Opal finds she can easily snipe the creature.
Reflex: 1d20 + 7 ⇒ (10) + 7 = 17
It seems to understand you, but you get the feeling that it does not care to speak back as it starts devouring crew from the previous ship it capsized, hungrily gobbling up sailors like popcorn shrimp.

Opal Windsong |

DM Amazing Red |

Luthor tries to coach the weapon crews to fire on the giant turtle.
Auto it and Freebooter's Bane
1d20 + 3 + 2 + 2 ⇒ (19) + 3 + 2 + 2 = 26
3d8 + 2 ⇒ (5, 8, 1) + 2 = 16
And it scores a direct hit, eliciting a roar from the beast.
Kal summons a wave and it pushes the creature back just barely. Only reason you got it was the nat 20. And I already added in the extra 8 from Opal.
It glares at the captain of the Sanbalot and tries to clamp its jaws on the semi-Ulfen.
PA: 1d20 + 18 ⇒ (9) + 18 = 27
4d6 + 10 ⇒ (1, 3, 1, 1) + 10 = 16
The crew start panicking but are still working as hard as ever to get away from the monster.
PCs up. For Opal's purposes, you are only within range for long range spells.

Luthor Stone |
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"I don't know what you're saying, but quit trying to talk to it and kill it." Luthor moves towards the creature.
AOO: 1d20 + 18 ⇒ (20) + 18 = 38
Confirming: 1d20 + 18 ⇒ (2) + 18 = 20
4d6 + 10 ⇒ (3, 5, 6, 6) + 10 = 30
The reptile takes another chunk out of the semi-ulfen.
He retaliates with a jab.
1d20 + 16 ⇒ (8) + 16 = 24
1d3 + 9 ⇒ (3) + 9 = 12

DM Amazing Red |

The turtle shifts over to take a swipe with it's claws at Kal.
1d20 + 18 ⇒ (19) + 18 = 37
3d6 + 10 ⇒ (4, 1, 5) + 10 = 20
1d20 + 18 ⇒ (8) + 18 = 26
3d6 + 10 ⇒ (2, 3, 3) + 10 = 18
He then bites at Luthor again.
1d20 + 18 ⇒ (11) + 18 = 29
4d6 + 10 ⇒ (1, 5, 3, 6) + 10 = 25
Battered, bloodied, but alive the Sanbalot finally breaks away from the creature and speeds on.
You must now skim through the outer edge of the titanic maelstrom that is the Eye of Abendego, tacking against the powerful northwesterly storm winds created by the cyclone’s counter-clockwise rotation. Navigating through the hurricane requires a successful Profession(Sailor) or Survival Check.

Kal Aldhemark |

Did the arrow hit, or do I need to try to recover it?
Kal heals himself and Luthor as they continue their journey, then tries to help with the next obstacle. Auto-aid whichever Luthor wants to use.
CSW on Kal: 3d8 + 8 ⇒ (4, 2, 2) + 8 = 16
CMW on Luthor: 2d8 + 8 ⇒ (8, 1) + 8 = 17
CLW on Luthor: 1d8 + 5 ⇒ (1) + 5 = 6
CMW on Kal: 2d8 + 8 ⇒ (7, 6) + 8 = 21
CLW wand on Luthor: 1d8 + 1 ⇒ (4) + 1 = 5
CLW wand on Luthor: 1d8 + 1 ⇒ (5) + 1 = 6
CLW wand on Luthor: 1d8 + 1 ⇒ (4) + 1 = 5
39 healing for Luthor. How far are you down still?
Storm: 8

DM Amazing Red |

The Storm keeps their course steady and while the Sanbalot suffers another setback.
Sanbalot loses 3 from their score while the Storm does not.
Once inside the hurricane however, things start becoming difficult.
1d100 ⇒ 89
Your vessels are blown over by the wind, flat against the sea. The vessel rights itself seconds later but avoiding falling overboard requires a successful reflex save.
1d100 ⇒ 19 Nothing happens
1d100 ⇒ 40
Steering becomes extremely difficult as your rudders jame. All Profession (sailor) checks are made with a –10 penalty until the rudder is unjammed, either via a successful Craft (carpentry) check or by casting warp wood or a similar spell.
And to make matters worse, A sheet of lightning strikes the foremast of
your ships, dealing 10d8 ⇒ (4, 6, 6, 2, 6, 8, 2, 4, 4, 1) = 43 damage giving both the broken condition. Your ships' maximum speed is reduced to half. If you succeed at a Craft (sails) or Craft (ships) check you can jury-rig the sails, suppressing the broken condition until the sails take more damage.
After that I need 5 more profession(sailor) checks.

Kal Aldhemark |

Recover?: 1d2 ⇒ 2
Reflex: 1d20 + 8 ⇒ (12) + 8 = 20 (Add 4 if it applies)
Kal hops in the water to try to unjam the rudder, then climbs back aboard and tries to fix the sails.
Craft (carpentry): 1d20 + 1 ⇒ (16) + 1 = 17
Craft (sails): 1d20 + 1 ⇒ (7) + 1 = 8
Can we keep trying to fix them?
Storm: 8

DM Amazing Red |

The Sanbalot gains a little ground but loses it quickly. No change.
The Storm speeds along, only suffering a small setback. Net gain of 2.
You must sail through the two concentric rings of Sharkskin Reef and around the towering spire of rock called Pinnacle Atoll. Steering the ship through both rings of the razor-sharp reefs requires four successful sailing checks.

DM Feral |

Opal tries to help as well.
Sailor: 1d20 + 6 ⇒ (10) + 6 = 16
Sailor: 1d20 + 6 ⇒ (17) + 6 = 23
Sailor: 1d20 + 6 ⇒ (9) + 6 = 15
Sailor: 1d20 + 6 ⇒ (5) + 6 = 11
Chubwart Sailor: 1d20 + 15 + 4 ⇒ (3) + 15 + 4 = 22
Chubwart Sailor: 1d20 + 15 + 4 ⇒ (10) + 15 + 4 = 29
Chubwart Sailor: 1d20 + 15 + 4 ⇒ (7) + 15 + 4 = 26
Chubwart Sailor: 1d20 + 15 + 4 ⇒ (17) + 15 + 4 = 36

DM Amazing Red |

Luthor: 1d20 + 13 + 2 ⇒ (8) + 13 + 2 = 23
Luthor: 1d20 + 13 + 2 ⇒ (10) + 13 + 2 = 25
Luthor: 1d20 + 13 + 2 ⇒ (9) + 13 + 2 = 24
Luthor: 1d20 + 13 + 2 ⇒ (14) + 13 + 2 = 29
The Storm's score doesn't change and the Sanbalot loses another 3 as they avoid the reefs.
You both emerge from the depths of the storm and discover that the majority of the other contenders have not yet made it out of the Eye. In fact, the only other ship in contention with the Storm is Captain Harrigan’s Wormwood! To the west, the Kraken cruises in the distance, the Master of the Gales on deck observing the race’s finish.
Give me a perception check and Kal can give me an additional perception check. The Storm and the Wormwood are neck and neck while the Sanbalot is 100 feet behind.

Kal Aldhemark |

Kal, hearing Opal's yells, casts his own spell in response. Control water under the Wormwood. It's now stuck in a whirlpool for 80 minutes and unable to leave by normal movement. No saving throw.
(I'm counting "the promise of a big baddie about to appear" as an ill effect manifesting for the purpose of the readying above.)