Most of the time I guestimate the time. Using diplomacy takes at least one minute, but the exact amount of time is up to the GM. Training is assumed to be done during the character's down time.
Keep an eye on the clock. Don't let the game get bogged-down over people just hemming and hawing over a puzzle, or an idea to solve a problem, or wandering around town. If they need time, say "I'm going to get a soda. Take fifteen minutes and then I'll go around the table and everyone checks in with me."
If the group is indecisive (which way do we go? I say we go that way! No, I say we go this way!) Then again, subtract yourself from the table, then return and go around the table. If everyone has deferred to a leader, then go to him last, and ask "which way?".
As for downtime in town, tell them "You're back in town with a few days to kill. What would your character be doing over three days? I'll go around the table, and everyone describe 3 days of downtime for your character." If they describe something cool or well-thought-out, give them 100xp per level (especially if it increases the group's reputation around town), or 10gp per level for something enterprising.
If it's a once-a-day sort of spell, let them roll once for each day they try it. "It's been four days, do you keep trying? Your DC is now 25. It might be time to go do research in the city, as you're not getting much done here." (Quest time!).
If someone has a really cool idea for an interaction, have them write down what they're attempting (gathering information from the thieve's guild for a specific mark) have them make a couple of rolls and set something up for the near future, or wing it and have it go down now. Handle these scenes last before starting the next adventure.
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Sometimes, when my players are dinking around too much I will get out my 1 minute hourglass and start fiddling with it. For some reason my players suddenly start to pay attention. I can't figure it out. :D
- Gauss
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I track time meticulously. I have a 9 month old campaign now and have made sure that I keep track of how many days each session lasts and make sure the environment matches (cold in the winter, hot in the summer).
long stretches of time are typically dictated by crafting.
Travel time I figure is 24-ish miles a day by foot. that is 8 hours of travel time. That allows for time to stop and eat, 10 hours for rest (which you have to have if there is a caster that will take watch) and for all the other things they would need to do. I actually listed out exactly how long a normal travel day would take, and 8 hours is almost all you have for travel.
So distance becomes a factor as well, but I typically put 3-4 days of travel between towns, that ends up being pretty good.
I am always flexible on training time, I make people take time to level every once in a while, but the game pace does not always allow for that. So I sometimes just let people level on the fly, and then sometimes I will I make things take a week or two for training.
Travel time I figure is 24-ish miles a day by foot. that is 8 hours of travel time. That allows for time to stop and eat, 10 hours for rest (which you have to have if there is a caster that will take watch) and for all the other things they would need to do. I actually listed out exactly how long a normal travel day would take, and 8 hours is almost all you have for travel.
http://www.d20pfsrd.com/gamemastering/exploration-movement
Travel time should depend on their speed of course. For some reason mounts take lethal from hustling.24 miles/day is only if they all move 30 ft/rd.
It is 16 miles if they only move 20 like a Dwarf, halfing, gnome.
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You should check out this podcast on 3.5 PRIVATE SANCTUARY: TIME MECHANICS (CRUNCH) . It's a great discussion.
