Content of the article: "Sleeping on the Go: A Case For Appyling the Sleeping in Armour Rules to Sleeping in Wagons"
One of my parties are currently undertaking a quest which involves transporting a package across the continent while being pursued by the forces of a dragon. As part of this quest, they've been provided with transportation in the form of an Arcane Wagon – a wagon driven by an Arcane Engine rather than by horses. So long as a party member is conscious contact with the Arcane Driver, the wagon will move at a fairly consistent pace. After only a few days of travelling, and after having been ambushed by some Kobolds belonging to their draconic adversary, the question came up.
Can we sleep while travelling on the wagon?
This was not something I had considered, nor something I had had to consider before. Of course, if a wagon is drawn by draft animals it has to stop at some point because they're not tireless, but my party essentially have a car. Now, it's a car without bedding and one that's established as being very uncomfortable to ride along in, but so long as one of them is awake, it'll move – and they could achieve this with the same principle that they could have rotating watches.
This suggestion had the potential of wrecking my plans a little, as I had calculated all distances on the assumption of ~8 hours of travel/day. But, there seemed to be no reason why they shouldn't, physically, be allowed to do so. However, it also didn't seem fair to me that sleeping on a bumpy wagon, with no bedding whatsoever and in cramped quarters should be as refreshing as sleeping properly. As I didn't want to deny them a long rest, I consulted the 'Sleeping in Armour Rules' from Xanathar's Guide to Everything. For the uninformed:
"..Sleeping in medium or heavy armour makes it difficult to recover fully during a long rest. When you finish a long rest during which you slept in medium or heavy armour, you gain only one quarter of your spent Hit Dice (minimum of one die). If you have any levels of exhaustion, the rest doesn't reduce your exhaustion level." (Xanathar's Guide to Everything, pp.77-78)
It seems to me that this can be perfectly adapted to this circumstance. After all, as my emphasis shows: the gist of this rule is sleeping in conditions that make it difficult to recover fully. You still get your 8 hours (or equivilent) and so suffer no short term penalties, but over time your characters may start to feel the penalties.
Now, I'm not saying this should be applied to trains, ships, airships or wagons with proper bedding, but simply that this is an interesting way of underscoring the physical toll sleeping on the go in rough conditions has, without punishing the party for moving and resting.
At any rate, as this is a sceanario I hadn't encountered before (and I've been DMing a while now), I thought my solution might be interesting to other people, but of course I'd be curious if there are any other solutions – official or otherwise.
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