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Driving to Montreal from Toronto tomorrow morning. Should I charge to 100% overnight?

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It‘s a conundrum. What are your thoughts?

Sure. It shouldn't be a conundrum. If having that extra range helps you complete your trip with a comfortable margin, then go for it. If charging to 100% is going to cause anxiety (which it shouldn't), use a Supercharger somewhere along the way or plug into 120 volts at your destination.
 
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There is nothing wrong with charging to 100%! The only real rules to follow are 1) don’t make a habit of it and 2) it is best to drive the car as soon as possible after reaching 100% so using Scheduled Departure, as recommended by others, is a good idea. But you really don’t need to sweat this one either.
 
For that distances you're going to have to make at least one supercharger stop along the way, so the extra starting charge won't make much of a difference. I'd shoot for Kingston since it's a 250kw V3, or figure out which one you'd like to stop at based on nearby restaurants. Then charge the vehicle at home accordingly. I'd probably just go for 90 to 95% and call it good.

The bigger question is, where are you going to charge in Montreal? I'm guessing this is a round trip back to Toronto (Tron'o? Am I saying that right?)? You could use one of the many superchargers in/around Montreal, but charging overnight could be a nice way to show yourself the luxury of owning an EV.

This is from PlugShare and I've enabled the Hotels filter so it's only showing locations that are in or near overnight lodging that you can charge a Tesla at. There are a LOT of options. Many of them are likely even free.

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Charging to 100% is worth it if you can get to your destination and then L1/L2 charge back to a full battery. The most important thing in winter is to supercharge with a warm battery, so charge when you reach your destination unless you have a L2 charger available to get you back to >80% overnight.
 
I have a place in Montreal and Toronto and go back and forth all the time; drive a ‘22 MS LR with usually another passenger and two pups.

No point charging to 100 as you’ll need to stop along the way. In weathers above -3 or so, I start at 90-95% and make a stop at Kingston (getting there with 10-15% buffer) and charge to 80 to finish the trip.

On days where it’s colder than -5, I do two stops, one in Cornwall and once in Belleville. I really hope that they open a supercharger between Cornwall and Kingston…
 
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Little late, but it’s ok to charge to 100% when needed, just don’t let it sit there for a while. The closer you can time your full charge to your departure time the better, but you don’t have to time it to the minute or something. 😜
 
Little late, but it’s ok to charge to 100% when needed, just don’t let it sit there for a while. The closer you can time your full charge to your departure time the better, but you don’t have to time it to the minute or something. 😜
I timed it so that the 100% was reached about 1 hour before departure. It's been such a learning experience. The "guess-o-meter" for arrival SoC is pretty good.

What I learned:
  1. Running multiple trip errands in Montreal on super cold days, really taps out the battery.
  2. Lead-foot driving really reduces the range
    1. Keeping it in the 115 KM speed with adaptive cruise or eve FSD is a good choice.
  3. Planning - It's all about better planning.
  4. So much more to learn
But dang, is this ever a great touring car!
 
Don’t be scared off by all the 100% warnings, there is nothing wrong with charging to 100% and even letting it sit at 100% for hours.

It is “better” to only charge to 100% when needed.

It is “better” to not leave it at 100% for hours on end.

What is really important is to NEVER let the car get to 0%. Although you can get away with that as well.
 
Hey y'all,
Thanks for the terrific feedback. Even though I had two previous Chevrolet Volts, this is "nuther level" stuff. Bonnie and I learned a bunch of cool things too. This "range anxiety" thing is only real if you don’t plan things out, but there are so many options. I never got to try the CHAdeMo adapter as I wanted to burn through my free SC KM's which were expiring March 22.

Interesting event: While on the highway at 115KM and in cruise control, there was a jam due to a truck jackknifed. "Nikola", slammed the brakes on when the cars ahead of us did the same. Très cool, AI!

Came home filthy AF, and took it to the touch free wash for a much needed shower. Overall uneventful experience, as it should be.