Naturally, any characters who are put in such a dreadful place are going to have only one thing on their mind -- surviving until they can escape. The question is, how to go about it?

Player characters are exceptional individuals practically by definition. They may have some special ability that enables them to escape, or they may come up with a cunning and original plan to get away. If it works for you, the GM, go with it - but don't make. It too easy. After all, the party magic-user may have a spell or two that could get him out - but what about the rest of them? What happens if his escape attempt fails -- can he get the spell back without his grimoires and library? Can he cast the spell at all without the proper components?

On the other hand, if escape seems impossible to your players, some NPC prisoner might present one of the following options for escape:

Tunneling

An exceptionally strong and patient inmate could tunnel out -- with the right tool. All that's required is a chunk of metal, but metal is in short supply in the Hole. Inhuman strength is required to tear a chunk off a grating (though that would make an adequate pick) and the only other metal around is the framework holding the glass panes above the garden. (It might be possible for someone very stealthy to sneak out of a cell, climb the wall and dismantle a part of the framework holding the glass to the wall - tricky, but it can be done.)

Once a tunnel is started, there's the question of hiding it. Putting your mattress on top of it works for a while, but if the guards decide to search your cell while you're up Top - you're in trouble plenty. Anyone who can make permanent illusions could do it, but that's hardly a common skill. Probably the best option is to start the tunnel in a distant and abandoned cell that the guards have no reason to check but that creates the problem of getting from cell to tunnel.

A additional concern is getting rid of the chopped up pieces of rock. Some can be scattered outside your cell door, but the guards would eventually notice a lot of gravel rattling around. A better option is to sneak it up top and drop it there -- over the side, if possible. Clever convicts may grind their waste stone into dust and simply let the wind blow it out of their hands each day up top.

The major question about tunneling is - where do you go? If you go out the bottom, you have the problem of getting past the wind (though a load of gravel, or a whole metal gate, might be sufficient to pull a heavy inmate down). A better option might be to tunnel into the garden or the Tower, in order to take the guards or even the Warden by surprise -- but that would lead to a hell of a battle...

Storm in the Mountains

The locks on the cells are not particularly sophisticated; after all, they're hundreds of years old. To someone with a bit of experience and something to use as a pick (a piece of wood or bone gnawed into the right shape, for example) they're about average. This means that many inmates have the skills to get out of their cells at will - and some have the tools as well.

However, getting out of your cell still leaves you few options. You can try to get down to the hatches on the bottom. However, there are no tunnels between the hatches and the cells - to get from one to the other, you have to go Topside, where the hatches are watched all day. They're not specifically watched at night, but then there are patrols over the whole Top. On the other hand, if you're trying to evade the guards at night, you can always tell which way they're looking.

Still, getting down to a hatch on the bottom raises the question of a controlled descent (or any descent). A lot of weight and not much surface area might do it - like five prisoners clinging together - but that makes it five times more likely that guards will be glaring at their retreating forms. (Going out a hatch for a controlled descent is a better idea than trying one over the side. Not only is the side watched, but the winds there are "reinforced" to pull escapees in. It's much easier to go down through a hatch.)

Another option for prisoners who can let themselves out is to wait for a storm in the mountains. All the prisoners know (or learn soon enough) that the Hole doesn't fly well in storms -- the strong winds tend to disrupt the pillar of air that holds it up.

Thus, the Hole can get as low as forty or fifty feet off the ground in a storm, and the wind that usually sucks jumpers to the bottom is greatly weakened. In a mountainous region, there's an even greater chance of the Hole being closer to a cliff or mountainside, making for an easier jump or descent. Of course, that does leave the prisoner nearly naked on a mountainside in the middle of a thunderstorm...

Waterspout

The Hole never flies over water. Never ever. If it did so, the winds that support it would suck up water and make a giant waterspout. This would flood the tunnels going to the hatches and pull the Hole down until it was only twenty feet above the surface of the water. Furthermore, anyone who jumped off the side would not get pulled back and stuck (the winds being too clogged with water). Finally, anyone who got out a hatch might be able to swim against the current (though this would be a feat of almost inhuman strength) and get down the waterspout to freedom.

All this, however, is predicated on someone being able to make the Hole go over a big body of water. It hasn't happened in the Hole's hundreds of years of flight; what sorcery could do so now?

Flying Away

One member of your party may have some magic that lets him/her or it fly away; what about the rest of them?

Someone familiar with flying, or even with sailing, might try to build some contraption to aid a controlled descent over the side. This plan avoids the incredible tedium of digging and is probably a little less risky than just grabbing something heavy, saying a prayer and jumping. A good flyer or sailor who had some sort of framework and fabric could use it to cut through the wind pillar supporting the Hole. That way, instead of getting sucked onto the underside of the Hole, he (or she, or they) would be squirted out the side and then be able to para-sail down (if incredibly lucky, and if no guards were glaring enough to set the glider on fire) or could take a slow spiral down inside the wind column.

Getting yourself over the side isn't all that hard; getting a glider built, and getting that over the side now that's hard.

First off, a glider will need a framework. The metal struts holding up the greenhouse roof might work, but they'd certainly be missed - and enough would have to be taken to cause at least one huge pane of glass to go crashing into the garden. (Of course, if you need a distraction ... )

A grate from a cell might also work but how to you hold it in the right shape? How do you get it apart in the first place? How do you keep the guards from noticing it's missing and where do you hide it once you take it?

Wood could also be used for a framework - but the only source of wood is the garden, and taking it in massive quantities would certainly be noticed. Taking small quantities gradually raises the question of concealment again. (A mattress might be OK for a while, but it's the first place guards search for contraband. After all, they were prisoners themselves.)

A final option is bone, which is strong and lightweight -- but acquiring it in sufficient quantities is difficult, to say the least. About one human skeleton would be required per glider, along with something to string it together.

Then, there's the question of fabric for the glider. An obvious option is the clothes of guards and prisoners. This could work, but it would take some doing; the weave on the cloth would have to be significantly tightened (anyone with any weaving background would know this and be able to do it). If two complete suits of prison clothes were picked apart, they'd yield enough material for one glider. On the other hand, it would take several days of effort to reweave them and sew them together.

An inventive option would be to use a pane of glass from the garden. The stiffness of the glass would remove the need for a framework, and it can be used (in a clumsy fashion) as a glider. The major problem is this; how do you get it down without breaking it? Once it's down, how do you control it? The panes are too wide for most people to grip (about eight feet square).

A third option is some sort of leather - presumably obtained the same way as a bone frame. It would take about two dead bodies to make one glider, and they'd have to cure for several days (assuming you got salt or - eeeugh! - chewed it) during which the stench would almost certainly attract guards. However, if these obstacles could be surmounted, leather would make a superb glider.

Killing the Warden

The most obvious option, and the most difficult. First, there's at least twenty guards; they can hole up in the Tower and glare fire down on prisoners from a distance. Then there's the Warden; if threatened, S/he can simply switch the gravity on the surface of the Top, making it difficult to get from the prison cells to the walls of the garden (to say the least). No, a big dumb frontal assault is a gamble at best.

Now, the prisoners do outnumber the guards by at least four or five to one; but getting a pack of selfinterested criminals to band together against feared guards with the power to crispy fry them is going to take a heroic feat of persuasion.

A sneak attack would make the persuasion easier; after all, the prisoners would love to get some payback. Sneaking up a tunnel into the Tower during the dark of night, boiling out to try to kill as many guards as fast as possible - that might have a lot more appeal than a suicide charge at the Tower. Especially if the PCs volunteered to be in front. It's still going to be a close fought, room to room battle though. And only the GM knows what dangers lie in the Tower...

Dropping the Rock

A final concern is this; if Moon Frost dies, the column of wind holding the Hole up dissipates. (She knows this and will openly tell it.) Dropping a thousand feet out of the sky on top of countless tons of rock is probably not a good survival tactic (plus, it's sure to royally irritate the country you land on).

Still, convicts are often noted for a lack of regard for the consequences of their actions. Some of the denizens of the Hole might consider a swift, noisy, incredibly destructive death preferable to rotting away in jail while an evil sorceress slowly munches on the best years of their lives.

One Final Thing

Anyone who does manage to escape the Hole will discover an unfortunate going-away present; the food was doctored with addictive agents. Going without it for a week causes nausea, dysentery and high fever. (Moon Frost thought this up to make punitive short rations even more unpleasant.) Have fun.

Hole in the Sky A Generic Fantasy Setting

Introduction
Welcome To Your Death
Dwellers in the Hole
Escape from the Inevitable