I-5 is not really possible due to a lack of chargers. CA-99 and 101 are both doable. 99 is actually shorter at 414 miles compared to 445 for the 101 route. However, with 99 you have a leg over the Grapevine that is 72.4 miles and has no backup charging opportunities.
The maps below were made with the PlugShare Trip Planner with filters set to only show CCS chargers.
I was originally going to say that 101 is the recommended route, but the more I think about it, I would probably go on 99. It's actually shorter and all of the charging sites have redundant chargers. On the 101 route, the E and F locations on the map are single medium power chargers. They can only deliver 62 amps DC (24kW) to the car while the rest can deliver 100-125 amps (50kW). Several of the other stops on the 101 route also only have one CCS plug, so if it's broken you're out of luck and will have to find an L2 to get enough juice to reach the next CCS charger. Anyway, in the best case, it's a 10 hour drive - 6.5 hours driving and 3.5 hours charging.
One trick to doing this kind of driving is to enter the address of the next charging station in your navigation. That way, you can see the distance to go and the car's guess at the range at a glance. You should generally drive with a buffer of at least 10 miles. If the buffer gets lower than that, slow down. Going over the Grapevine is going to be stressful because the car is going to have a terrible guess at the range while you're climbing. Hopefully you have a SEL with cruise control because the best approach would be to set the cruise to 65mph and leave it there until you get to Wheeler Ridge and the I-5 / CA-99 split. Then you can really judge how much energy you have left and possibly drive faster the rest of the way to the chargers at the Bakersfield Wal-Mart.
If you're going to do this drive in hot weather, there's a good chance that the car will start limiting the power for driving and charging. The battery pack does not have any active cooling and freeway driving and fast charging both generate heat in the battery pack. You will want to keep an eye on the small power meter in the instrument cluster. For the southbound return trip, you may encounter power limiting when you're climbing out of the central valley and the car may not be able to hold 65mph uphill. I'm not saying it will happen and I've not seen an actual account of this trip in an e-Golf, but it could happen.