i'll perhaps elaborate a bit more with mine:
95 monte carlo, 3100, 4T60E
i take very long highway-bound trips fairly often.... when the air temp is ~50*F or less, the trans temp never really gets above the 150*F point. the same cruise when it's ~80*F out, i'll watch the trans temp slowly creep up to the coolant temp(roughly ~198*F), but it takes quite some time(an hour or so of cruising at 70MPH).
creeping around town on a hot day, i'll see temps get above my coolant temp, but i've never gotten above ~220*F that i know of.
that's with an unmodified cooling system. at times i consider adding in an auxiliary trans cooler, but it's probably not necessary. current fluids take higher temps much better than they did back in the day.