Link: https://goblinshenchman.wordpress.com/2020/11/30/simple-ish-chase-mechanic-2d6-race-to-a-target/
Main text from blog post:
Relative separation of parties
Determine the initial relative separation separating the parties (between 2 to 12): if this is a random encounter, roll 2D6 to set the relative separation. The ‘separation’ could be nautical miles, 10s of feet or perhaps even bar stools in a tavern!
The two outcomes
:: 2 (or less) = caught / on top of each other
:: 12 (+) = escaped / far away
The chase
Each turn determine if the relative separation between the parties increases or decreases. To do this, roll 2D6 :
:: if the roll is below the current relative separation, the separation increases by 2 units;
:: else the current relative separation decreases by 2 units (i.e. the parties get closer);
:: optionally, a tied roll means the relative separation stays the same
Repeat until the ‘caught’ or ‘escaped’ result is obtained.
Speed
One party might be faster than the other, if so roll 3D6 (instead of the 2D6 above):
:: if the pursuer is faster , select the highest 2 rolls;
:: if the fleer is faster , select the lowest 2 rolls
This is effectively an ‘advantage/disadvantage’ mechanic.
Conditions
Conditions, like wind speed, could come into play (e.g. a row ship chasing a sail ship). If so, perhaps add a +/- 1 modifier.