Assaulting a Fortress (PF)

[Oncoming Storm]

Alright, so next session, our group will be assaulting the floating fortress of one of our major enemies. Let me set the scene:

The setting consists of numerous floating islands, kilometres across, held aloft by magical fields above a layer of nearly impenetrable stormclouds. The location we are at (the capitol of the main empire) consists of several dozen of these islands connected and/or freefloating around a central beacon of energy. There are a number of noble families, each with their own island which they rule more-or-less autonomously. The BBEG is the head of one of these noble families, having usurped the position from one of our PCs parents (via torture and murder.) In the last couple years, he has more or less isolated himself on this island, only accepting occasional shipments of food (they grow most of their own.) All attempts to infiltrate the island have failed so far, and there is no reliable intel about the layout of the main fortress, except that it is large an near one edge of the island. The BBEG has a VERY sizeable military force, with at least three- to five-hundred Gryphon Knights (presumably cavaliers) based on 3 separate outposts on the island, with multiple exits to each (so blocking them off is infeasible) as well as an unknown number of mercenaries, including both arcane and divine casters of at LEAST 9th level (they have been seen using 5th level spells.) The entire island is warded against scrying, and the BBEG has a reputedly vast amount of money, so anything goes for traps and even permancied spells. To make matters more complicated, we want to do this with minimal loss of civilian life (there are several thousand civvies on the island) so dropping the island out of the sky is out of the question. We are reasonably confident that if we take out the BBEG himself, the enemy will capitulate, or at least give us breathing room.

Our party is level 7, and includes a (severely-and almost aggressively-unoptimized) scrollmaster wizard, an Inquisitor, A gish Oracle, a Cavalier (aforementioned aggrieved relative,) A druid, and a gunslinger/pistolero. None of us are particularly optimized, though the Cavalier effectively has a Gryphon mount.

For resources, we have 5000 gp or so for materials, as well as an ally willing to supply us with low-level potions and scrolls. We don't know quite how far that generosity extends, though. We also have a team of crack troops (about 20) trained for anti-gryphon combat (but not stealth.)

The plans we have thought of so far:
1. Infiltrate the fortress and assassinate the BBEG. has the benefit of bypassing the legion of class-levelled troops. Downside is that if we're detected, we're likely toast, and we have no info about the inside of the fortress at all. Initial infiltration would use one or more gliders with invisibility cast on them+occupants. Unfortunately, if he has guards with permanent arcane sight (or something) this method is far from foolproof.

2. Pretend to hand over the Cavalier, use the opportunity to get within striking range of the BBEG and unleash hell. Has the benefit of having relatively few moving parts, and leaves the possibility of withdrawing (leaving the cavalier behind:smalleek: if the odds are utterly suicidal. However, we have no guarantee the BBEG will come to meet us himself, nor that if he does so, it will not be accompanied with a legion of spellcasters, retainers, and knights.

3. Load a glider (or more than one glider) with copious amounts of explosives and alchemist's fire, and fly them into the fortress, ejecting before impact. Using invisibility spheres to render the gliders invisible beforehand, it would be difficult to effectively counter the initial bombardment, and might give us a window to get in and clear the obejctive before the legion of troops can be effectively deployed. Downside is that the mobilization time on Gryphon knights is incredibly quick, and starting our op with explosions would CERTAINLY get all of them in the air in a hurry.

So, I'm just wondering if anyone can think of something that I've missed, insofar as tactics are concerned. I'd thought of using some kind of wind control to ground the gryphons, but most of the more useful magic is 5th-6th level at least.
please note that any shenanigans that depend on weird interpretations of RAW are unlikely to fly with this DM.

thanks!

[Oncoming Storm]

no one? I'm really feeling like this is a situation where our likelihood of success is slim at best.

[Quiddle]

Ok I'm game. I like plans one and two, do you guys have decent bluff scores, illusion magic, disguise self, and all that stuff that you would need for an infiltration?

[Quiddle]

Your druid can turn into a tiny animal, you could turn in the druid (have them think he is some petty thief, a regular criminal with no magic). Then in the dead of night have your druid wild shape into a tiny animal and drink a potion of reduce person(hidden on his person) allowing him to slip through what ever they have him stuck in. Have the druid start a prison riot then open the gates for the rest of your force and in all the chaos go kill the bbeg and win.

[avr]

The party seems generally non-sneaky, at least from the class list. If sneaky people have tried infiltrating and failed, plan 1 seems like 'Intro to the Great Escape from prison' scene.

Plan 2 has potential though at best you get to fight the BBEG and his bodyguards with their full kit. If there's anyone for hire who might be able to throw extra dispel magics at them to remove buffs get them on board.

Plan 3 wouldn't work for any group sneaky or not. I cannot endorse it.

Other means of sneaking in might involve planar travel or scry/teleporting. No, you don't have inherent access to these but you might be able to buy scrolls or services.

[Grollub]

Ultimately your group needs to decide on tactics... Stealth or Assault.

Assault.

your glider plans sound good.. you could also use the gliders to specifically target 1 gryphon tower and bomb the hell out of it. either set to destroy that 1 tower ( after which you retreat ) or as a major distraction to glide in invisible on the main tower to attack the BBEG.

Handing over Cavalier.

While initially this could be a good plan. With an enemy as well equipped as you would expect from the BBEG, you are putting yourself at the mercy of the GM. I would expect the BBEG to come in, expecting a trap, and a full attack force with him. HIGHLY doubtful he would come in with a minimal compliment , unless your GM is generous. I guess you could also use this tactic in a ruse, lure them out.. and assault main base while he's away =D

Stealth

Your plan to infiltrate the fortress and assasinate, prob sounds the best plan. If you have any extra resources, I would focus them on escape, in case the plan goes south.


You could mix and match anything you've come up with , with the stealth plan to confuse the enemy more, and increase success chances ( ie.. you could arrange to go in on a stealth run, maybe triggering the firebombing run on an isolated part of the fort to cover you, or just cause chaos )

[GoldenGecko]

there are several thousand civvies on the island

Would it be possible to become a citizen / masquerade as one? With these kinds of defenses, assault seems suicidal and covert infiltration seems very risky, so why not infiltrate the island by becoming a part of it?

Also, from your speech, it appears that you have the means to remove the island from the sky and are loathe to do so only for civilian life; why not find a method of forcing an evacuation, even if only of the civilians, before dropping the island?


If you can't break down the fortress, smoke the people out -- defenses are only useful when somebody is behind them.

[Oncoming Storm]

first, thanks for all the responses!

Goldengecko- infiltration is possible, but at best it leaves us in a similar place to our initial infiltration. From what we gather, civilians mostly don't have castle access, so we'd still have to sneak in. might be an opportunity to gather intel first though...still, the whole island's had very little traffic in the last few years, and we don't know what the civilian population's loyalty is like. If the BBEG is a decent lord (no indications to contrary) they might be loyal enough to point out outsiders.

As far as civilian casualties and island destruction goes...each island has a large, magical stone at it's core which generates the field keeping it aloft. destroy the stone, island falls. On populated islands, these are often the most heavily guarded part of the island (for good reason) and would almost certainly be encased in admantium in an AMF. not terribly feasible. The other suggested plan was based on the fact that this island is under other islands--If we blow off a sizable chunk of the island above, immense structural damage would ensue from large chunks of debris moving at terminal velocity. Hence massive civilian casualties.

avr-It's not quite as bad as it looks from the class list. The party has two sneaky members --myself (the oracle) and the inquisitor both have very respectable stealth scores, him due to high dex, myself due to having acquired certain aspects of the vampiric template, including the racial stealth bonus (incidentally, I can also gaseous form and spider climb as SLAs 3/day, so that also goes to the stealthy.) The druid can stealth passably, due to ability to turn into an innocuous animal.

Quiddle-I like your plan, but the problem is that it's not really an open the gates type of situation--they're on a floating island, constantly patrolled by gryphon knights. I suppose that could work for information gathering about the layout of the place, though. As for social skills, we have the bases well covered. Illusion less so, but given the guy's wealth I expect permancied detect magic on sergeants at the very least, so walking in reeking of illusion might set off alarm bells.

[Quiddle]

Got a bag of holding? Have your party load into the bag you go gaseous and fly, find the bbeg (easier again at night), return to normal form, open bag of holding(letting out party), kill bbeg and get out the same way you got in.

[WhiteLycan]

Get a hold of animate dead. Send one of your explosive gliders to attack one of the forts as a distraction with skeletons and zombies dressed from head to toe to make them think they're under serious attack. They'll call for backup from the other forts and then your small group can get inside the main fortress with the BBEG.

A helpful spell against the gryphons would be earthbind, I think that's what it's called. It's in spell compendium. Causes flying targets to fall from the sky.

[Oncoming Storm]

Only real problem with that is that once they're mobilized, and realize it's a feint, they WILL come after us. We'd have maybe 2-5 minutes to get in and out,which is stretching it.

[Rentaromon]

i have an idea....

the threat of death is far more powerful than death itself. Threaten to bring down massive rocks from above, make a show of force by dropping rocks in an area where there or no civilians. Have people inside the city as a civilian spread rumors of people finding lots of small rocks around and on their houses(while also spreading rocks around at night). The fear will force the BBEG to make some sort of decision, and once he makes a move you can respond better, you cant just let him sit back and do nothing.

Maybe you can force him to talk to you to save his people. Maybe he will try to attack the island above him, but that would threaten him with war with the other islands who have a massive positional advantage on him.

Maybe he will try to enforce his skies and leave other areas less protected.

Maybe he will try to move his island, potentially waiting massive resource on a fake threat.

Maybe he will do nothing, and you can make his people think he cares nothing for their lives.

[Lightlawbliss]

Do you know of any way to disable and/or change the floating for just his island?

How about digging through island?

[Akolbi]

Do you know of any way to disable and/or change the floating for just his island?

How about digging through island?


i have an idea....

the threat of death is far more powerful than death itself. Threaten to bring down massive rocks from above, make a show of force by dropping rocks in an area where there or no civilians. Have people inside the city as a civilian spread rumors of people finding lots of small rocks around and on their houses(while also spreading rocks around at night). The fear will force the BBEG to make some sort of decision, and once he makes a move you can respond better, you cant just let him sit back and do nothing.

Maybe you can force him to talk to you to save his people. Maybe he will try to attack the island above him, but that would threaten him with war with the other islands who have a massive positional advantage on him.

Maybe he will try to enforce his skies and leave other areas less protected.

Maybe he will try to move his island, potentially waiting massive resource on a fake threat.

Maybe he will do nothing, and you can make his people think he cares nothing for their lives.

This could be mage better with a moderatly liberal interpretation of Hallucinaroy terrain.

else, capture a high officer in the defence force, and geas him into killing the BBEG.

if you need scouting, arcane eye should work.

charm monster would raise a nice army, if you could swing it that way, paired with animate dead or constructs you could get a decent attack force.

the best bet, however, is probably making an illusory army, and coming in under an invisibility sphere on the other side of the castle. if you use the arcane eye scouting idea, it would work better, also, investing in some seige weapons for a few hirilings would be a great way to make it look real.

or you could feint the army out, and crush it with a bunch of the big floating rocks, see how the GM feels about having "rocks fall, everybody dies" used on him. ;)

[Slipperychicken]

the threat of death is far more powerful than death itself. Threaten to bring down massive rocks from above, make a show of force by dropping rocks in an area where there or no civilians. Have people inside the city as a civilian spread rumors of people finding lots of small rocks around and on their houses(while also spreading rocks around at night). The fear will force the BBEG to make some sort of decision, and once he makes a move you can respond better, you cant just let him sit back and do nothing.


If the PCs can take down the island, see if you can threaten the BBEG with that.

[Oncoming Storm]

Taking down the island is not an option-or at least, it would be far more difficult to do than simply ganking the BBEG. Furthermore, if we threaten it, we put him on alert. Which is bad. Currently, as far as we know he doesn't know we're coming for him, and I would hate to blow the element of surprise so easily

As I said, scrying is a no go thus far for the island.

Also, I did mention the three to five HUNDRED Pc-class levelled knights riding griffons, right? They're all probably at least level 3 to 4, judging from their reputation, and that many enemies? Could probably just nat20 us to death with crossbows if they had to. Doesn't even count the multiple lvl 9+ casters in the area either. I'd really have to say that any straightforward assault is a no-go.

Finally, I feel like the personal threat of the BBEG himself may be being discounted a little here. He's a mid-to-high level Cavalier with absurd WBL, so 'just' killing the BBEG (especially if he's battle-prepared) isn't a trivial task in itself. We might be able to do it in option 2 with the help of a surprise round to knock out his defenses and escape methods, but in a straight up fight, he's not going to just fold the moment we shoot an arrow/spell/oversized greatsword at him. A metric ton of explosives might do it though...hm.

Maybe if we did option B, then had someone standing by with one those explosive gliders to hit him if he shows his face outside/make a distraction/hole for us to escape. we'd need some pretty hefty abjurations though, to make sure we didn't end up fried along with him.

[Quiddle]

I assume the dm won't let you just sneak in and coup des gras him. He'll want some big fight right?

[Oncoming Storm]

I assume so. This has been foreshadowed for quite some time, and is a main motivational point for two characters (mine and the Cavalier.) Anticlimactic is also not generally his style. Additionally, my char would be..less than thrilled if the guy got to die so easily as that. (He has several months of ceaseless torture/a severed arm to repay.)

[Drachasor]

I think you guys are going to need some more levels before this is really feasible.

If you're at least level 9, then the Wizard could theoretically use Prying Eyes to do some scouting. They can move 16 miles per hour (constructs can "run" without limit). Send them in pairs with one far enough back to just keep track of the other one, and the follower returns if the one in front is destroyed.

That should at least get you a better idea of what the basic defenses might be like.

At level 7, the Wizard could hopefully learn Shadow Projection (http://www.dxcontent.com/SDB_SpellBlock.asp?SDBID=865). With other spells that could allow him to investigate and see what the defenses are like. A healer would need to stand by since it might well end with the shadow being destroyed.

Similarly, at level 9 Possess Object (http://www.dxcontent.com/SDB_SpellBlock.asp?SDBID=1098) could be used for recon.

Given that there's been no one to successfully infiltrate this place that you know of, you should assume it is extremely, extremely dangerous. This is not something you can just rush in and hope it will work out. So you'll probably want to make sure that Teleport spells will work both going in and out of here (or Plane Shift at least). Have at least 3 or 4 escape plans in case things go wrong. Again, this is much easier in 2-4 levels.

[Oncoming Storm]

I LIKE the shadow projection idea. Any idea if it's traceable back to us in any way?

waiting is...somewhat infeasible, from an In-character perspective (and because it would be somewhat rude to thumb our noses at the DM's crafting of campaign opportunities linked to our character's backstories.)

There have actually been two infiltrations that managed to get IN-they just lost contact and were not heard from again afterwards. OTOH, as far as I know the teams were all composed of Alchemists (not exactly the sneakiest class) I do agree that any infiltration would need at least 3 potential escape routes, with one 'panic button' (like planeshift.)

[Beldar]

The main difficulty here is lack of information - you don't know what the enemy setup is well enough to exploit their weaknesses (there are *always* weaknesses of some sort).

If you knew more about them, especially their defenses, you could be more confident of everything (especially infiltration tactics, but also escape and attack plans).

So, with scrying blocked, how do you learn more?

There are several ways. Start with low-payout low-risk approaches, so you hopefully learn a bit with little to no risk. Knowing a bit often enables ways to learn more.

It helps that they don't know yet that you are out to get them - maintain that advantage while you can.

So, start with the D&D version of observing from a safe distance using a telescope. Though in this case use the Eyes of the Avoral spell from the Book of Exalted Deeds. The fluff text of that says that you can see like an avoral does. The text of an avoral says they can see details out to 10 miles.
So you should be able to get a pretty good idea about daily routines etc.
Just get on an island above them and watch.

The more you know, the more possibilities will open up. You may discover that some citizens go off by themselves occasionally. This could open up the possibility of useful contact (more on that in a moment).

Another way to "scry without scrying" is to send in animals to observe. Have the druid make some animal friends. Doing it via spell is easiest, but it is completely possible to just buy a 'pet' and make it your friend over time with treats, good treatment and use of the Handle Animal ability - and the effectiveness of all that is multiplied by the Speak with Animals spell.
Even if the enemy is doing some very effective things to detect magic or detect scrying, a normal non-magical pet you've spoken to will not show up on their 'radar'. Flying pets can go in for a look & come out. When they come back, use Speak with Animals to find out what they learned (And possibly Detect Thoughts to root around in their memories to get your own take on what they noticed).
Using a few flyer missions, you should then be able to step it up to some walking animals you can insert via glider (Ideally made in some disposable way, like via Conjure Ice Object - so the evidence of insertion melts).

Between what they see and hear you should be able to get some idea of what is safe & what isn't.
Maybe there are uninhabited, unpatrolled areas. Maybe they pounce on certain kinds of activity & ignore others. Who knows what will turn up. But as you learn more, something will turn up.

Then step it up a notch - send in flying pets with Chain of Eyes on them & see what happens. Similarly, send in an invisible pet & see what happens. If the enemy pounces on them, you get an idea of what kind of things they can detect. If the Chain of Eyes stops working in a certain area, but they still come back and report, then you've learned they block it but don't track it down and kill it.

Then see if a pet dog, polymorphed into a bird, can fly in & fly out. If so, you know that shapechanging isn't automatically detected. That gives you options.

Have a pet bird drop a Listening Coin (Bard spell you may have to hire someone to cast for you - basically a microphone) in & see if it is detected, and/or if it reports information. If it seems to work, try listening Coins in a few locations & see what you can learn.

Then take a page from history & see if you can find a local you can subvert to your cause. As with most spy recruitment, this starts with a lot of observation, trying to find someone who is discontented, or who is corrupt and can be bought or blackmailed. When you identify a subject, always start small - asking small favors that seem innocuous enough. Get a history going of them giving you help - help which increments up & up in usefulness & you can gradually get to a point where they tell you anything (either because they trust you by now, or because they know you can incriminate them by revealing whet they have done for you so far).

Information from a local will likely reveal quite a bit & quickly.

You can approach a local either by an anonymous note left for them (by a pet dog instructed to do so), with a system of anonymous rewards (gold left in a certain hidden spot) or even, if polymorphing turned out to be safe, the druid himself (show up as a bird or squirrel and observe, then after learning enough to make it possible, try passing yourself off as another citizen, or guard, or hired caster etc - whatever you know enough about to have a chance of pulling off successfully).

In learning about them the above kinds of ways, you can hopefully find ways to help your assault.
For example, you can pre-position stashes of escape gear and disguises, in case your eventual foray into the area goes bad.
You may also find something exploitable, such as rival factions within the defenders. You could then work on harming one faction while framing another faction for it. That can at least get them focusing on something other than defending against you. And it could, in extreme cases, result in them fighting each-other all-out.

You may learn other weaknesses, such as them having no clerical magic. In that case, spells like Contagion become your friend - stealthily infect some defenders with a contagious disease and wait for it to spread. This could weaken the defenders, or it could result in them doing something like contracting for clerical casters to come in & fix it. You may be able to finagle it so you could be one of those contracted casters.

So, in short, when you know little, there are few options. And the more you know, the more options you have. Both for how to attack, as well as how to escape should your attack go bad.

As for your eventual attack - the setup sounds like one designed to force you into an approach other than basic assault - they are way too strong, relative to you, to just charge in & fight them. And if so (ie, if it has been setup to make you think of something other than straightforward assault), then there will be other ways to sneak in & carry out your mission. You just have to find out what they are.

So, once you know enough about how to do so successfully, I imagine you will end up doing something like sneaking in, bypassing guards & fighting the BBEG in his bedroom at night - or at least attempting that & getting to a certain point before being discovered & having a basic assault from that point on.

Just in case of discovery (ie, if your infiltration becomes an assault), you will want to set up options, such as some way (Sending scroll, released carrier-pigeon - whatever will work) to tell NPC helpers to release the explosive gliders at a part of the islands defenses where you are not.
Give the defenders competing emergencies/attacks to deal with & at least some of them will not come after you. The more competing emergencies/distractions you can set up in such a case, the better. That gives you a better chance.

[souridealist]

My thought is that you want to find ways to weaken his defenses before you hit the fortress. Ideas, and I'm mostly just bouncing them into the ether to see if they spark anything for you:

- See if you can "boy who cried wolf" the guards. After two weeks of things that look like attacks and aren't, anybody's going to get lazy. Illusions, send yourself or the druid flying around with a sackful of your magic items to create the impression of a VAST ASSORTMENT of magic auras about to attack, light extraneous campfires, stuff like that. Bluff them out as much you can.

- Attack their supplies. You probably can't do anything to water sources if there are any divine casters on the island, but food is more vulnerable. You and the druid can fly in and burn the crops in the fields, or hole up and cast create water until the plants are drowned. A starved army doesn't fight well, a people deprived of food to feed the army is going to cause the BBEG some troubles as well, and the strain on the civilian population can hopefully be relieved by train after you liberate the place.

- If your druid has any charisma modifier to speak of, get creative with Wild Empathy, especially if your DM will let you make wild empathy checks to influence animals while speaking to them in animal form. (I don't know if you can usually do this or not, I'm afraid, but it's worth asking.) Horses and cows can stampede, wreaking further havoc on crops, fences, possibly even palisades or fortress walls, I don't know. Dogs and cats can soil food supplies or keep soldiers up all night. Hunger and fatigue penalties for your enemies can't possibly hurt your chances. Rats and mice (who I expected to be vermin, but they aren't) can chew through bowstrings, saddle girths, maybe armor fastenings and scabbards... That's not even getting into how thoroughly creepy it would be to have all your animals suddenly lose it. Also, there's no way the local anti-mouse-and-rat forces don't know their way around the castle, and the local mouse-and-rat forces might have some ideas too. So: intel!

- See if you can burn any of the griffon stables? This would be hard, obviously, but it sounds like a fair bit of your enemies' defenses are hinged on those griffons. If you can injure even a significant portion, well then.

- I thought of introducing dead, disease-bearing animals (a real siege tactic people used) but that would probably 1) cause not insignificant loss of civilian life, even if you did this mostly around the military outposts, and 2) cheese off the druid no end. Also, not sure where the alignment system stands on primitive biological warfare. Still, it's a thought.

- You're partially a vampire. If there are small guard patrols (one or two), can you go all creature-of-the-night on them?

That's what I've got for now. Let us know what you end up doing, I'm fascinated.

[Haldir]

The main sticking point to me is the ridiculous number of flying and magical troops.

The good thing is you have a druid and a wizard. Both of which can use magic to scout- summon air elementals, use flying and tiny animals to get into areas, Wildshape into a griffon and plant the druid in the stables as a spy.

Use enchantments to force grooms and servants (there are grooms and servants for a big noble and upkeeping all those animals) to help you commit acts of sabotage. Maybe you poison one group of griffons via a compelled groom, your druid infiltrates one group of griffons and uses fear and animal control effects to neutralize them, and your anti-Griffon squad engages the third group.

Use invisibility and the gliders to then slide the rest of your team into the BBEG. Compel servants, cooks, or locals to let you know where the clerics and wizards are housed, these are the people you should target for espionage the most (poisoning/boobytrapping/spellbook stealing.) Hitting them while they are in the middle of daily spell prep would be best.

[Beldar]

Here are a couple more thoughts.

Another way to get information from a local is to kidnap one, ideally in a stealthy way.
Say one night a lone guard falls off the rampart of his island in the sky. Whoever investigates it should never know that in fact he was pushed off the wall by a druid that changed back from bird form when he wasn't looking (possibly assisted by a scroll of Grease or Ice Slick), with the druid then escaping in bird form again, & somebody waiting some distance below with a readied action to use the Feather Fall spell. If you capture him, great, there are many ways you can find out info. If you fail to capture him, you can still learn a little via Speak With Dead.

You could manage similar things with just about any kind of lone guard, or possibly even a small group of griffin riders, with a little luck and the right setup.

Then add Charm Person & they'll tell you everything. While they are your prisoner, you have enough time to cast it again & again until they fail eventually their saves.

As for your early missions, sending in a bird to listen - Your object is to observe what is normal behavior so you can mimic it (for infiltration), and also to hear whatever you can that will be of use.
So have them seek out things like little old ladies chatting with each-other over the back fence as they hang up the laundry - they will chat about literally *anything*. If there are any usable scandals, rivalries etc, they will likely know and chat about it.

Further, if the BBEG got his position via evil and torture, then his people are very likely to be unhappy. What kind of person you are comes out & shows itself constantly in the things you do. So it is very likely he abuses his people in small ways (at least small ways - maybe major ways) which have, over time, given them quite negative feelings about him.

In such a case, finding local informers should be easy.
But it also opens up other attack options.

You could, for instance, find a way (like a scroll of Fabricate) to create enough gliders for them to all escape one night. That would require a fair amount of coordination & planning, but, if successful, could leave you with a much better position.
For instance, without anybody on the island but guards, nobody is growing food for them. So they have to do something or starve.
And with no innocents in the way of harm, more options like bombing the island with big rocks become available.

[Oncoming Storm]

Firstly: Holy Crap! that's waaaay more help than I was expecting! Thanks!

As far as alignment goes, the party has 2 good characters (1 being the Cavalier) 3 Neutrals (all Chaotic Neutral) and 1 LE inquisitor. So we're all over the map in terms of alignment.

The main issue I have with ANYTHING that attracts attention is that right now, we have the element of surprise. They haven't been attacked at all in the last couple of months, and as far as we know, they don't even know we're on the island. I'm worried that they'll tighten security even more if they get suspicious. Still, animals are a great idea. Getting them in might be tricky (the winds are fairly strong, and the distance is not insignificant--any flying creature smaller than medium will probably have difficulties.

The druid will absolutely have a FIT if we start destroying crops and livestock. Even an attack on the gryphons might be problematic. OTOH, infiltration via gryphon wildshape is an amazing idea and I can't believe it didn't occur to me.

One thing I forgot to mention is that there is a fairly substantial clerical presence on the island, which may or may not be favorable disposed to him. Unfortunately, it's the NE church of the blood god. Still, maybe they're in contact with the other chapters of their church somehow? If so, it'd be an excellent source of info. hmmm.

Sadly the extent of my vampiric powers are as follows: Gaseous form and spider climb as SLAs, DR 5/Silver, the ability to drink blood, and the addition of Charm Person to my spell list. I initially did have dominate person 1/day, but the DM came to his senses with a bit of creative demonstration on my part.

If we have to do some kind of siege warfare, then the illusory attacks and things would be great for irritating them. Eventually, they'd probably start sending just patrols to investigate disturbances instead of fully mobilizing, which would give us another couple of minutes of grace time once the alarm is raised.

[Haldir]

Do not forget to use compulsions to plant spies and double agents. It will yield large returns.

[Drachasor]

I LIKE the shadow projection idea. Any idea if it's traceable back to us in any way?

waiting is...somewhat infeasible, from an In-character perspective (and because it would be somewhat rude to thumb our noses at the DM's crafting of campaign opportunities linked to our character's backstories.)

There have actually been two infiltrations that managed to get IN-they just lost contact and were not heard from again afterwards. OTOH, as far as I know the teams were all composed of Alchemists (not exactly the sneakiest class) I do agree that any infiltration would need at least 3 potential escape routes, with one 'panic button' (like planeshift.)

It shouldn't be traceable, especially if you wear something to disguise your shadow.

I wasn't sure whether the DM was pushing this or the players. If the DM is, then yeah, it probably is going to be level appropriate. Perhaps your infiltration will be more long-term.

I think a Hat of Disguise is probably a very sound investment. Being able to disguise yourself as a guard, random townsperson, or whatever is a very useful skill, especially when you get a +10 to your check.

Suggestion is a worthwhile spell too, as its effects won't be noticeable, whereas, I think Charm Person would get noticed when it wore off. Detect Thoughts can also be useful. There are a number of good non-scrying divination spells, so I'd go through the spell list. One short-range escape option is a scroll of Dimension Door, though this is only good for the caster and two others -- the Druid should be able to run away pretty effectively on his own though.

For the Druid, beyond Wild Shape spying, some useful spells are: Negate Aroma (if the enemy uses anything with Scent), Speak with Animals (they might have intel), Speak with Plants, Meld into Stone (better if he can somehow carry the rest of the party, but you probably can't afford anything that allows that).

If the enemy has never seen you before, the it might be effective to plan on getting jobs in the enemy castle and surrounding area. They don't likely have any sort of ID system, so lying about where you are from should work. If you have anyone actually trained in disguise they could even replace someone if they have a Hat of Disguise (assuming magic detection isn't often used by the enemy -- wizard might need to use a polymorph spell and Arcane Sight to investigate this possibility, though the Druid with Detect Magic is another option).

As far as guerilla warfare goes...well, any organized bureaucracy is quite vulnerable to Explosive Runes -- use Magical Aura to help disguise it sooner or later. Though it is best to use a variety of strategies so the enemy can't expect any one thing...ideally ones where defending against one leaves you open to another, or ones that strain limited resources.

If the enemy is someone other than Daniel Jackson, a distraction before the main attack is a good idea. A large fire or something that looks like a main attack to draw enemy forces -- perhaps 4 or 5 such things, can make the actually big bad more vulnerable.