Standing watch is a staple of fantasy travel. Here is basic advice for doing it in Old School Hack. Giving people six hours of sleep is generally enough, and that is two of the three watches–so people can stand one watch and still get a full night’s sleep.
To stay awake during a watch requires a Brawn or Awareness test.
- First Watch. 9 p.m. to midnight. Difficulty 6.
- Second Watch. Midnight to 3 a.m. Difficulty 10.
- Third Watch. 3 a.m. to 6 a.m. Difficulty 8.
Generally horses have an Awareness/Brawn of +2, if weary characters rely on them to wake. If you are not woken for your shift, you can test at +2 difficulty to see if you wake up on your own. And if more than one person is standing a watch, and at least one stays awake, that one can keep the others awake (or let them sleep) as desired.
So the watches cover 9 hours, leaving 15 for the day. Assuming 1 hour to break camp, one hour for lunch, and an hour to make camp, plus time for breaks, and inserting the general fuzziness to the schedule in an era without watches, that assumes 10 hours for travel in a day.