You are a Pirate
Rolls
Secret Roll
The next day, a storm pushes the Chianti closer towards the coast of an island. Seemingly from thin air, a large ship appears behind, it flys a black flag with no other markings. The crew aboard the mystery ship seem racing back and forth, readying the cannons. It is clear it means to engage the Chianti. Shira is a bold captain and calls all hands on deck, man the cannons, and to prepare the grapples. She knows the Chianti is outgunned, and feels like the only chance of victory would be to board the enemy. A few volleys are traded, and the Chianti is within 50 ft of the enemy ship. Grapples are loosed and many make their mark. The two ships are currently intertwined.
Rolls
Initiative - (1D20+3)
(19) + 3 = 22
Rolls
Initiative - (1d20)
(19) = 19
Pasquale will ready a cast of Bless, he positions himself so he can try to get all the PCs in range just before the action starts.
Rolls
Initiative - (1d20+1)
(9) + 1 = 10
Rolls
Initiative - (1d20+6)
(11) + 6 = 17
With Pasqual's casting of bless reaches Roche and Zunis, but There is too high up. Zunis' shield goes off, and he waits till the ships are closer.
Shira shouts out "Pull! Pull you scallywags!", her voice rings out across the deck of the ship as much of the crew scramble to a rope and heave together in an attempt to win this tug of war against the enemy frigate.
Others have also swing across to the enemy ship similar to Theren and Roche.
They are successful as the boat gets towed in, now only about 25ft away. Some crew members loose crossbow bolts, and the enemy returns fire.
Theren
Zunis'
Roche
Enemy crew
Pasqual
Chianti crew
Rolls
Reeling in the boat - (1d20+2)
(15) + 2 = 17
Advantage for multiple hooks - (1d20+2)
(3) + 2 = 5
Edit: Aw
Rolls
Intimidation (including advantage if you feel it fitting to give it to me) - (1d20+1, 1d20+1)
1d20+1 : (2) + 1 = 3
1d20+1 : (3) + 1 = 4
Still I'm rigging: Theren would turn holding on back to the rigging seeing if there is anyone close by before throwing a dart towards them.
Bonus: Spending Ki to use dodge action. (Disadvantage to attack Theren.)
Rolls
Acrobatics - (1D20+5)
(8) + 5 = 13
Attack roll (Shortsword and dart have same bonus) - (1D20+5)
(17) + 5 = 22
Damage (Dart) - (1D4+3)
(1) + 3 = 4
Damage (Sword) - (1D6+3)
(5) + 3 = 8
Rolls
Rapier attack, damage - (1d20+6, 1d8+4)
1d20+6 : (17) + 6 = 23
1d8+4 : (3) + 4 = 7
Sneak attack - (2d6)
(22) = 4
Roscoe manages to easily swing from the ship, becoming a miniature Tarzan as he hopes to another rope, slices it loose, and swings down through the enemy deck, lashing out at the chaotic movements. As he moves into the enemy crew, he is also attacked by the mob, but he jumps off an enemy, simultaneously slicing the poor girl's neck and launching Roscoe out of the way of a reaching mace. Roscoe heads towards another poor soul, pulling a similar maneuver, to launch off, correcting his swinging course while leaving death in his wake.
The enemy ship is a menagerie of races and peoples, some hanging from the rigging, some racing up from below deck, and others popping off spells. There seems to be an aura of still quite from one member on this enemy ship, as he bellows out a stringent command, "Cut those hooks!"
as he says this, he slices a taught rope with his large cutlass, resulting in a group of friendly pulling crew members next to Zunis flying backwards on top of each other. He continues to move forward seeming to disappear into the battle. Other enemy crew members hear his call and attempt to follow suit, racing to nearby hooks. Only one more rope snaps from the sharp bite of an enemy blade. Others grab some loose rigging themselves and swing over to the Chianti, brandishing their swords as they cross the open water.
Rolls
Theren attacked - (1d20+3)
(18) + 3 = 21
Disadv - (1d20+3)
(20) + 3 = 23
Roscoe attacked - (1d20+3)
(10) + 3 = 13
Attack against the ropes - (1d20+3)
(7) + 3 = 10
Attack against the ropes - (1d20+3)
(5) + 3 = 8
Theren damage - (1d8+3)
(5) + 3 = 8
Rolls
Crossbow shot at the commander, damage - (1d20+1, 1d4, 1d8+1)
1d20+1 : (7) + 1 = 8
1d4 : (4) = 4
1d8+1 : (2) + 1 = 3
Scythe swing at an enemy, damage - (1d20+5, 1d4, 1d8+3)
1d20+5 : (7) + 5 = 12
1d4 : (1) = 1
1d8+3 : (6) + 3 = 9