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100% trip on road trip (multiple times)

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So I’m going on another road trip this weekend and I was curious about the charging part.

We charged our car to 100% for our road trip but should we charge it again to 100% on the half way point before coming back?

Our last road trip was short so we only did 100% to start off and then up to 80% only at charge stations.
 
It depends ons several factors; how far you are going, frequency of SC available, and desired arrival state of charge (just to name a couple).

For my first few trips I charged to 100%. After several more trips I realized that I could start the trip with 80% and still make it with the same amount of charging stops.

One thing to try is play with A Better Route Planner (ABRP). Put in your destination and play with the starting charge percentage to see how it affects the trip. I would only charge to 100% if absolutely required to make it.

For most of my trips now I try and stay between 5% and 70% (unless I really need to stretch range). Note the supercharging is fastest at lower states of charge.
 
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For a trip that you have taken before, try charging to between 80% and 90% instead of 100% before you leave if only because it takes less time to charge to 90% than waiting to charge up to 100%. The ideal charging scenario when on a road trip is to charge as quickly as possible. This means arriving at the Supercharger with the Tesla battery preconditioned for Supercharging and the battery state of charge ~20% or less. When Supercharging the Tesla vehicle will notify you when you have enough charge to reach your destination (i.e. this could be on the drive Home.) It is generally ~2X as expensive to use a Supercharger as when charging at Home so at your last Supercharging stop you might want to only charge until you have enough range to reach Home. Maybe add an extra 10% for unexpected delays or bad weather/roads. You will find that colder weather increases energy consumption. Expect an additional 15% to 20% energy usage for the same trip you took earlier this year.
 
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Only if you have a leg of the trip that needs a 100% charge to reach the next supercharger without "white knuckle" driving / battery capacity left.
yeah this ^^. I've had my car almost 8 years and can count on one hand the # of times I've charged to 100% to get to the next location on road trips.

Just charge enough to get you to the next location with 10%+ ish buffer.