(Tempe is up.)

Quote from Brian_Avery >>

Tentacle 3 let's go of the mast and follows tentacle 4 as it recoils beneath the waves with a loud angry splash.

 
Damage for Tentacle 3 as it starts it’s turn within Randall’s Spirit Guardians Aura, if it matters:  19

Tempe satisfied with his spell cast flame-blade and moves to attack the fifth tentacle Attack: 11 Damage: 6

Attack: 18 Damage: 14

which ends the spike growth spell.

Tentacle 3 and 4 are considered to be defeated and will not rise above the waves again.

(Randall is up. After that Tentacle 5 will finish round 2 and I will post an updated initiative order without T3 and T4.)

Randall:

His Spiritual Guardians swirling around him, Randall strides over to the fifth tentacle and strikes at it with his glowing mace!

Lightbringer Attack:  Attack: 24 Damage: 8

He then casts a quick spell, and a holy mace springs into being, attacking the tentacle also.

Spiritual Weapon:  Attack: 28 Damage: 13

When the tentacle starts its turn, the Spirit Guardians torment and burn it, trying to drive it away from the ahip:

Spirit Guardians:  17

After suffering a barrage from Randall, Tentacle 5 still tries to grapple the ship:

Grapple: 19

Initiative Order:

Tentacle 1
Pepin
Tentacle 2
Petcan
Zenodor
Tempe
Randall
Tentacle 5

Tentacle 1 tries to grapple the ship:

Grapple: 11

(Pepin is up.)

Pepin decides that the guiding bolt and force ballista seemed to work fine so he shoots both of them again. Guiding bolt into the face of the monster and the force ballista on tentacle 1:

Guiding bolt: 26, damage; 13 radiant.

Force balista: 27, force damage and move 5ft away from balista: 9

Tentacle 2 tries to grapple the ship:

Grapple: 9

The overly huge tentacle writhes and roils as it attempts to gain purchase on the ship and threaten to instantly submerge the vessel beneath the waves and certain doom. Nearby crew valiantly fight with weapons, tools, and whatever is at hand to fight it off, and are soon joined by several more crew as they succeed in not only holding it at bay but driving it back. The ship lists from side to side under the assault of the massive tentacles and bobs precariously on the surface of the waves but remains on the surface for now.

(Petcan is up. Zenodor is next.)

Petcan keeps up the fire bolt attack on the nearest tentacle 

Attack: 20 Damage: 15 

The conjured dragon continues rending (twice)

Attack: 21 Damage: 14 

Attack: 15 Damage: 15 

And a breath attack DC 16 dex save for half 6 

Z continues to blast at the grappling tentacles from above:

Blast 1: Attack: 13 Damage: 6

Blast 2: Attack: 10 Damage: 10

Z uses his bonus action to try to telekinetically shove the tentacles away (forgot I had this): STR 16

(Telekinetic - Shove

As a bonus action, you can try to telekinetically shove one creature you can see within 30 ft. of you. The target must succeed on a STR save (DC 16) or be moved 5 ft. toward you or away from you. A creature can willingly fail this save.)

Flying above the deck Tempe again attacks tentacle #5 with his flame blade,  trying to get it off the ship 

Attack: 15 Damage: 16

Attack: 27 Damage: 10

Ki Attack: 22 Damage: 13

The tentacles writhe in agony and a burbling screech can be heard from below.

(Randall is up.)

Randall:

As the fifth tentacle retreats, Randall moves towards the other two on the ship, trying to place himself between them so that they both are subjected to his Spirit Guardians.  Calling down spiritual fire on the one that has the tighter grip (Tentacle 1 since it rolled the Crit grapple), Randall also sends the glowing mace of force to strike it!

Sacred Flame on Tentacle 1 (DC 17 Dexterity Save to negate):  11

Spiritual Weapon on Tentacle 1:  Attack: 24 Damage: 11

Spiritual Guardians on Tentacle 1 on its turn (DC 17 Wisdom for half):  27:

Spiritual Guardians on Tentacle 2 on its turn: (DC 17 Wisdom for half):  20:

WIS save: 16

The tentacles recoil and the mighty Octopus-like creature sinks beneath the waves.

(some things about the combat for the curious... nothing serious, just for those who like a peek behind the scenes)

Seeing the creature go down, Pepin immediately checks the bottom of the ship for any damage, before going to the surface and doing a check in the sides of the ships (he can Also walk along water due to his ring). If no structural damage is to be found he will find the rope and climb onto the deck to check on how it stands there.