We just finished our first road trip in our S85 (pano roof + air suspension, no tech package) and had no issues. Car performed like a champ the whole time.
We charged to 90% (around 240 miles) on our NEMA 14-50 the night before, then drove up on a Friday afternoon. It was around 85F the whole time according to the car and we used custom eco A/C and cruise control on and off the whole way, using navigation (and Rdio for music) off one of our Bluetooth-connected mobile phones. We stopped at Tracy Nissan (found on plugshare.com) for a potty break. We didn't need the charge but we went ahead and plugged into the free J1772 for about 10-15 minutes and gained maybe 3 miles of charge.
We stayed overnight at a Hilton in Sacramento. They had no EV parking or available power outlet, said the only hotel in town that did was the Marriott. We were a little nervous to see if we'd lose 8 miles overnight but I don't think we lost any. I meant to mention to the hotel that if they installed a NEMA 14-50 they might get more Tesla owners staying there but didn't get to it.
We did our first ever Tesla Time in the Hilton parking lot with a guy from the UK who seemed impressed with the 265-mile range and the price tag. He said he'd never seen a Tesla in the wild before. We didn't see any Teslas on our travels, though we did see many Nissan Leafs and of course Toyota Priuses and, to our surprise, one GM Spark EV.
In the morning we drove about 25 miles farther east to the Folsom supercharger at the premium outlets mall. Technically this was out of our way. No problem finding the superchargers using the on-board map with red icon showing us their exact location. There were four spots, only one of which was occupied by a red S. We plugged in with 46 miles of charge estimated left, and within a minute or two were getting an astonishing free 265 miles per hour of charge at 360V and 250A. We meandered over to the TCBY and had some vegan froyo then meandered back 52 minutes later with the car topped up to 229 miles of range. The red S had left and in its place was a black S and the other side of us was another black S.
On the way back to Sacramento, we stopped in Rancho Cordova to show the S to some family friends who have a Jaguar. They said the Jag is a lot noisier than the S and everyone in the car stopped talking when I pressed the accelerator to show them what it was like getting on the freeway. I didn't have to put it all the way down to get everybody's attention but I didn't press it to the metal either (didn't want to get a speeding ticket or cause an accident, heh).
Next morning (Sunday) we mapped ourselves back home via the Fremont supercharger. I must say coming south over the Benicia/Martinez bridge was like driving through hell--smokestacks everywhere pumping smoke into the air, which was a uniform gray haze--portents of a grim and terrifying future we hope to avoid. Arrived at the Tesla factory after a much shorter drive back; at least half the bays were empty. With some relief, we plugged in with 33 miles of range (first time we'd ever seen the range bar turn dark yellow) and went inside the little lounge. When we came back about 10 minutes later, we noted that another Model S had parked and was using the adjacent supercharger to ours; the power supply for both of these parking spots had its fan running loudly and our S had its A/C running to cool our batteries as they charged. We unplugged with about 120 miles of range and headed home.
All in all, it was totally smooth sailing. We did experience some mild anxiety about not plugging in overnight and deciding when and where to charge, but having an open supercharger located every 150 miles really just solved it completely. Experiencing the supercharger cemented something visceral; it's one thing to read about it, another to actually plug in and watch the miles tick on. Every 8 seconds, another mile. Wow, just wow. Also, for what it's worth, Google Maps on our phones had a lot of trouble keeping track of where the hell we were, constantly rerouting us for bogus reasons (assuming we were on a frontage road when we were actually on the freeway, telling us to do a U-turn because it thought we were going the opposite direction, etc.) whereas the Model S's onboard map always showed us in the actual exact location where we were.