(Yes to this as well, I'm going with Brian's plan. I had suggested pairing up our scouts but if DragonDenn wants to go for it alone then that's toootally fine.)

I'm fine with paring up the scouts, just Rubin would have wanted to make sure the others knew he would be invisible.

As you approach the quay, an armored human mounted on . . .something approaches in the water.  You can see 5 other figures on the landing, which is within 30 feet of you now.

"Oi, who are you?  What are you doin' here?"

"New recruits. From Red Larch. Didn't you get orders we would be arriving today?"

Deception (if needed): 8 

The figure pauses, looking closely at you, then snorts.

"Idiot.  You really think the first place new recruits would be sent is here?"

She motions the rest of her troops forward, and charges forward on her water mount.  As she moves, you catch a glimpse of a large shark with a saddle on it under her.

Initiative:

Rubin: 9

Kethra: 21

Jairus: 5

Davian: 3

Tyde: 15

Reavers: 13

Knight: 23

Fathomer: 6

(Tyde is up.  The knight is right next to you, the rest are about 30 feet away on the landing.)

Tyde will cast Web to catch as many as he can on the landing in a 20 foot area. (not sure how they are positioned?)

DEX save vs. DC 14 when starting your turn or first entering the webs or restrained until you break free.

Where is Rubin at when his turn comes around?  he would not have entered the area with light, and should still be invisible if still able to be in darkness.

(We'll say you're in the back of the boat.)

Tyde, you can catch all of them that are on the landing.

Reavers: 22, 19, 13, 18

Fathomer: 7

The fathomer seems to melt away, turning into a serpent composed entirely of water.  It slithers effortlessly through the webs, and swims towards the boat, ending its turn around 10 feet away.

(Note that the one reaver won't be restrained until its turn.)

(Jairus and Rubin are up)

I didn't think Rubin was ever in the boat.  He was swimming to scout.

Rubin sends several crossbow bolts at the leader of these clear enemies...

Attack: 11 Damage: 17

Bonus action Attack: 5 Damage: 14

Dread Attack: 20 Damage: 14  Dread Damage: 1

Quote from DragonDenn >>

I didn't think Rubin was ever in the boat.  He was swimming to scout.

(Yeah, same here. I was hoping for a stealth or a perception roll, not to just run straight into these guys...)

(It would be kind of hard to be stealthy enough in a boat.  Against enemies very well acquainted with water and boats.  Rubin being in the water wouldn't change much since he'd be invisible.)

Rubin unleashes a hailstorm of bolts on the leader, turning the water red and nearly dropping her in one go.  She manages to twist a bit to lessen the impact of the first bolt, however.

She urges her shark forward, and strikes at Kethra with her lance.  Her shark will bite at Rubin, able to see him due to its blindsight (she can be in range of both since lances have Reach).

Vs. Kethra:

Attack: 23 Damage: 4

Vs. Rubin:

Attack: 12 Damage: 9

(This is assuming Rubin is only 10-15 feet away from the boat, which I believe is the case.)

The four reavers all toss javelins at each of you but Rubin.

Vs Kethra: 15 Damage: 7

Vs Davian: 10 Damage: 4

Vs Jairus: 7 Damage: 5

Vs  Tyde: 6 Damage: 7

(Everyone but Rubin is up.)

Tyde will cast Acid Splash at two of the reavers who are within five feet of each other (if not, then just one of them).

DEX save vs. DC 14 or they each take 1 acid damage.

Quote from LordShadowthorn >>

(It would be kind of hard to be stealthy enough in a boat.  Against enemies very well acquainted with water and boats.  Rubin being in the water wouldn't change much since he'd be invisible.)

(Could you please tell us this ahead of time instead of rolling initiative? Then we could've nicely told you that it was only Rubin and Davian scouting ahead by swimming, not on the boat just like last time. Being forced to run headfirst into two encounters we were carefully approaching (twice in a row!), is really dangerous for us at this difficulty, DM. Please give us a little grace next time.)

Quote from LordShadowthorn >>

The four reavers all toss javelins at each of you but Rubin.

(One of the reavers is still restrained from Mr. Tyde's web spell and will have disadvantage to attacking. Could you let it be the one tossing javelin at me? oO)

Using a swordfighting stance with her maul, the pale blue eyed girl takes the hit from the knight for the sake of the party, only to be astounded at the giant toothy maw that surfaces to bite the Rubin that she could not see before.

"We're with Grimjaw, you fool! This enough proof for you?!"

Maul to-hit (reckless attack): 25 Damage: 13

If this is does not kill the knight, Kethra attacks the knight again and again. If not, she'll start punching the shark.

Flurry of Blows 1 (reckless attack): 20 Damage: 4

Flurry of Blows 2 (reckless attack): 13 Damage: 5

Edit: Oh wowowow, 2 critical hits....

Maul critical hit: 4

Flurry of Blows critical hit: 2

(Why aren't you adding any mod to your flurry of blows again?  Also, both were encounters that couldn't be easily avoided through stealth.  The ghouls were lurking there specifically to ambush passers-by, and the knight and her group were on watch.  Rubin would have been unseen were it not for the shark's blindsight.  You might have been able to gain a little more time had I been paying more attention to scouting, but it wouldn't have mattered much.)

The first blow easily downs the knight, and the two punches hit the shark solidly.

The restrained reaver tries to break free instead of chucking a pointy stick at Kethra: 16

But barely doesn't manage to (forgot to add strength mod of 2, but still not enough.

Two attempt to avoid Tyde's lovely glob of acid (assuming one of the targets is the restrained one):

Dex: 7, 10

One succeeds, the other does not.

The fathomer sees that the shark is targeting someone in the water, but can't quite make out what it's biting at.  It attempts to grab Rubin in its coils anyways . . .

Attack: 5 Damage: 11.  If it hits, he is grappled.

The one reaver tries to get out again: 14

The other 3 begin swimming towards the boat, but have to dash to make it far enough.

Jairus fires at the shark.

Attack: 22 Damage: 5 SA: 4

Attack: 12 Damage: 9

Davian heals Kethra for 8 hit points, and stays in his human form.

(Everyone else is up again.  I'll close recruitment tomorrow so there'll be more than 3 of you again.)

Rubin targets the shark...

Attack: 24 Damage: 8

Bonus action Attack: 9 Damage: 7

(If the reaver's made it to the boat by dashing then this is my turn:)

Tyde will cast Thunderwave on the the reavers.

CON save vs. DC 14 or take 13 thunder damage and be pushed 10 feet away from me.

I use my Sculpt Spells feature to protect Rubin and 1 other ally if needed.

(If the reaver's have not quite reached the boat by dashing then this is my turn:)

Tyde will cast Shatter on the reavers.

CON save vs. DC 14 or take 15 thunder damage .

I use my Sculpt Spells feature to protect Rubin and 2 other allies if needed.

Rubin would actually be out range of the thunderwave, since he's a little ways off in the water.  That said, all but one of the reavers is in range, as well as the fathomer.

Reaver con saves: 21, 20, 8

Fathomer con: 21

Many of the reavers are injured, but none too badly yet.  Only one is pushed away from the boat.

(Kethra is up)