Hey Darryl,
I saw that you are signed up for both the SoCal and the San Diego challenges. I'm going to guess that you're referring to doing the original six peaks from the SoCal challenge: Mount Wilson, Cucamonga Peak, San Antonio (Mt Baldy), San Bernardino, San Jacinto and San Gorgonio.
First, this has been done in less than 48 hours a number of years ago by two guys.
If you're looking for efficiency, I'd probably do them in this order:
San Jacinto (furthest east)
San Gorgonio and San Bernardino (you can connect these two via the ridge, if you are supported)
Cucamonga Peak and San Antonio (Mt Baldy) – these two are close, but I wouldn't bother trying to hike between them. Just do them as two hikes.
Mount Wilson – This is the lowest and furthest west.
This order travels roughly from the east to the west, and groups hikes that are close to each other. As I mention, San Gorgonio and San Bernardino can be done together (I've done this as an overnight backpack trip), but to be efficient, you'd start and end at different trailheads. If you have a support vehicle, that would work.
Speaking of which, I strongly advise having a support team to handle the driving between trailheads, and bring one or two changes of shoes and socks.
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