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Timing / Timelines

I have trouble determining how much time events in my novels take. Especially when multiple important events are happening at once. I never know without seriously thinking about it whether enough time has passed for this character to appear here or for that character to have travelled there etc.

I tried making a timeline recently but am still finding it hard to estimate how long certain things would take.

Does anyone else have this problem? Any tips on how I can resolve it? (I'm writing fantasy, by the way, which makes things a bit harder ).

I've done my share of timelines for long fantasy stories. Mostly in learning what not to do.

If you never mention that City A is 158 miles from City B, then no one can whine that you made the horses take too long to get there. If you don't say exactly how many days it took them, then there's nothing to whine about there, either. "A few days later, as dusk lit the sky behind them, the trio rode into Village Q, tired and dusty." "Few" covers anything reasonable for short riding trips, IMO. Three to six days, and that's a lot of leeway.

I see in books how they say "it's two days' ride to X", and then you don't have to worry about how far it is. You've just said how long it'll take, and that's all that matters for your plot, most likely. Unless a character's into cartography or he's got an army to march somewhere, he won't care how many miles/leagues/li/millimeters it is, either.

You didn't say what you're having timeline issues with; here's some random fantasy figures that might help.

Battles between two people usually take less than an hour. Sometimes only a few minutes.
Pitched battles in a war can take days, even weeks.
Any flying through the air, you won't want to go faster than a car on the freeway, unless you have goggles and warm clothes. Wind chill is awful up high where it's already cold.
An army can travel between 15 and 30 miles a day in good weather, depending on terrain. In bad weather or snow, maybe a mile or two a day.
A horse and rider can cover a huge range of distance a day, depending on terrain. An impressive horse could make up to 100 flat miles in one day. If you have several days' travel in a row, 20-40 would be more reasonable.
People usually stride between 2-3 miles an hour if they're walking a long distance on flat ground. Running can be around 5-8 miles an hour if your character's in a hurry. If they're outside, keep in mind the terrain.

I use calendars too. My long timelines are several months or years' worth of calendars. Sometimes I like to put on my characters' birthdays and other stuff that won't enter into the story at all, just to make it feel more real.