"Oh ooooh, lemme think.  Manny, you could make me a whale again and I can smash the boat to bits and eat everyone again.  That was so fun last time!"

"I'm happy to start shooting them from here. hmmmm We could just blow up the ship and move on in a sense... Not my preferred method but quick and easy to hit some vital spots and watch it sink. It wouldn't guarantee we'd get the cultists but a step back for them nonetheless." 

Genren says, bow drawn as he keeps eyes on the deck of the ship waiting to take out his next target. 

Ronkur charges up his gauntlet, the reddish glow building and spreading, barely contained.  'And I can make them arrows burn when they hit, follow up with a few blast of mine own, not sure it'll sink 'em, but it'll get their attention for sure.'

(ooc Ronkur has Flame Arrows prepped and could follow up with firebolts from the air 

(If you're decided on a course of action, go ahead and post your surprise action and roll for initiative. I'll take your average Init score vs the anchorites score and just make it easy on us =)

'Be careful about too much fire, guys - there could be prisoners on board... That said, let's get them dealt with!' Mandred says with a grin, also shaking his head at Tallow's desire to be a whale again 'Maybe next time, Tallow, or if they run...'

Manfred mutters a few words, and points towards the front ballista, his lute adding its own meolody... 'Wakey wakey...' he says as a sudden intense ringing sound emanates from that point...

(Shatter has a 10ft radius sphere, so he'll get the ballista and try and include both orcs if possible. DC 16 Con save for the orcs, versus 8 thunder damage)

(Initiative: 17)

Ronkur casts Flame Arrows on 12 arrows in Genren's quiver and then takes off into the air on his floating disks, hovering about 50 ft above and behind the boat.  Following Manfreds cue, the artificer pulls his arms as far back as they can go and then brings them together in a swift and sudden movement, muttering in an unintelligible stream of numbers and letters that have no apparent meaning. 

The war machine on the stern of the boat is surrounded by a roiling, boiling wave of sound (Shatter Con 19 or 12 half on a save)

Initiative 9

DM Rolls:

Genren shoots an arrow at his foes on the ship staying high up on his perch for the time being. 

Attack: 20 Damage: 14

Elven Accuracy: 13

Sneak Attack: 22

Initiative: 19

(@genren, you've got flame arrows in that quiver if you want 'em - extra 1d6 fire damage)

Tallow gives Manny a disappointed look before erupting with delight at the start of battle.  He casts Tasha's Caustic Brew in a line attempting to hit both creatures near the ballista.  Dex save 16 or 22

Initiative 3

Wakka init: 24

The party wins the initiative challenge! You get another round of attacks =)

Manfred casts shatter from his spot ~50' away to catch the ballista and the two anchorites. (DC16 Con: 6; 15 or 8 dmg)
Ronkur flies up and aft, targeting one of the mangonels and an anchorite on the stern of the ship. (DC19 Con: 19 or 12 dmg)
Genren (needs to specify his target, or at least the deck...)
Tallow moves forward 30' and unleashes a stream of caustic acid! He can only target one creature, though. (DC16 Dex: 4 or 22 dmg)
Wakka ???

(Whoops sorry!) Genren would be targeting the anchorites who were by the giant undead with the glaive. Adding Fire damage here: 2

Next round of attack:

Attack: 17 Damage: 13

Elven Accuracy: 13

Sneak attack: 17

Fire Damage: 2

Ronkur fingers a rune inside his glove and a shimmering field of energy surrounds him.  Leaning forward, the armored gnome accelerates towards the stern of the ship, blasting away at the anchorites near the mangonels as he comes screaming in.

Action: 

Firebolt Attack 1: 17 Damage: 20

Firebolt Attack 2: 28 Damage: 17

Bonus Action: Defensive Field for 10 temp hitpoints

Move: Fly forward and down 50 feet, moving to get within melee range of the stern of the ship 

Tallow is almost vibrating with excitement as he shrieks out to his companions, "Watch this!  I learned something new!"  He casts Fireball at 4th level at the ship where Manfred had cast Shatter Dex 16 or 33  He will also spend one sorcery point for Transmuted Spell to change the spell damage to acid.

Surprise Round
Manfred casts shatter from his spot ~50' away to catch the ballista and the two anchorites. (DC16 Con: 6; 15 or 8 dmg)
Ronkur flies up and aft, targeting one of the mangonels and an anchorite on the stern of the ship. (DC19 Con: 19 or 12 dmg)
Genren shoots an arrow at the anchorites on the forecastle. (29 damage!)
Tallow moves forward 30' and unleashes a stream of caustic acid! He can only target one creature, though. (DC16 Dex: 4 or 22 dmg)
Wakka ???
Anchorites(-59; -8 // -0; -0; -0; -0 // -6; -0) -- Ship (-??) -- Ballista(-30) -- Mangonels(-12; -0)

Round 1:
Manfred
Ronkur accelerates towards the stern of the ship, blasting away at one of the anchorites.
Genren hits the other anchorite on the forecastle with his 2nd flaming arrow.
Tallow casts Acidball at the ballista forward, melting it and snapping the cable! (DC16 Dex: 4 or 30 dmg) the other anchorite also goes down, its flesh melting away in the gob of acid...
Wakka
Anchorites(-59; -62 // -0; -0; -0; -0 // -43; -0) -- Ship (-??) -- Ballista(-60) -- Mangonels(-12; -0)

Manfred's first round action?
Wakka - are you still with us?

Manfred starts to move closer to the ship (25ft) to get into position for the next round, then casts Shatter again in the same location..

(9 thunder damage, DC16 CON ST)

'You've got this Genren. Some great shooting there!' (1d8 bardic inspiration for Genren)

• DC16 Con: 16 or 9 dmg fwd.
• The iron brazier mounted on the mainmast contains with an ever-burning orb of flame hurls a magical ball of fire that explodes in the middle of the 3 group! (1,3=Manfred and Tallow; 2,4=Genren and Wakka) The two in the targeted group must make a DC 18 Dexterity saving throw. They take 24 fire damage and 38 necrotic damage on a failed save, or half as much damage on a successful one...
• The four anchorites on the main deck transform into giant boars and charge down the gangplank towards the two groups, two at each pair. (10'/15' away from Manfred/Tallow, and 40' away from Genren and Wakka.)
• The last anchorite on the stern casts lightning bolt at Ronkur, still floating to the stern. Make a DC12 DEX saving throw, taking 24 lightning damage on a failed save, 1/2 if successful.

Round 2!

Ronkur Dex save 4

The gnome takes the lightning blast head-on and dives straight down towards the offending anchorite.  He charges his gauntlets with Booming Blade before swinging and shoving at the defender.

Attack: 16 Damage: 11
Attack: 10 Damage: 11
Bonus Action: Telepathic shove, DC 17 Str or move 5 feet back Booming Blade if they move after that

Looking up at the brazier, Manfred casts Dispel Magic on the brazier (cast at 4th level, so anything 4th level or lower is automatically dispelled, rolled 12 if it's a higher level effect)

'Go get them, Tallow. I recognise your abilities!' (1d8 bardic inspiration for Tallow)

He then moves to within 5ft of the boar moving towards him, to deny it a chance to charge...