I've run a million of these things so, here goes....
You need a minimum of 1.5" sch40 conduit underground. It must be adapted to EMT (metal) above ground and must be sealed to remain water tight (10 mil plumber's tape) at the junctions. You may also use sch 80 conduit in some applications, but Metal will cover all codes.
You must have a minimum of 18" to the TOP of the pipe from finished grade. I usually dig my trench 24". You cannot have more than 270 degrees of bends in your run - you have a 90 coming out of your box and another running up into your other box - this leaves 90 degrees to play with so it really should be a straight shot. It makes it a bitch to pull if it isn't.
The minimum conductors for a 100 amp service are: (3) #4 and (1) # 6 THHN and AWG. The # 6 is ground, or you can pound two more 8' rods at your garage and not run the extra wire.
DO NOT FORGET TO MARK ONE OF THE #4'S FOR YOUR NEUTRAL BEFORE RUNNING THEM IN THE CONDUIT.
Always shut everything off and remember that some buss bars are still hot EVEN IF THE BREAKERS ARE NOT!
You could just run the conduit and leave a pull strap in it - and your electrician could run and energize the wire.
please don't kill yourself.
Thanks,
Vic