Here is what I would do on my overnight trip with first-timer friends:

1) Leave San Diego at 3-3:30 AM on a day of hike (alternatively, leave one day earlier to get more sleep)
2) Arrive to Lone Pine before 8:00 AM, collect permits at the ranger station
3) Have breakfast at the Alabama Hills Cafe (failure to do so significantly decreases the chances of reaching the top)
4) Start hiking from the Portal no later than 10:00 AM
5) Arrive to the Outpost Camp in early afternoon
6) CAMP at Outpost (more on that below)
7) Have early dinner, bed time by 7-8 PM
8) Start a summit bid from the Outpost Camp at 2-3 AM
9) Summit before lunch time at a relaxed pace
10) Return to camp and celebrate, spend another night there (you don't want to drive home after a long day in the mountains)
11) Descend in the morning, have a yummy brunch at Alabama Hills Cafe, and drive home.

The advantages of camping at Outpost instead of the Trail Camp are 4-fold:

1) Lower Elevation = better sleep = (arguably) better acclimation
2) Instant access to excellent water, as opposed to filthy pond at the Trail camp where people wash their dishes. There is running water at TC, but it will be much harder to find in August after a dry winter
3) Less traveling with a heavy pack
4) More privacy and protection from trees

These advantages outweigh the disadvantage of adding a few extra miles on a summit day. Over the past 12 years, I had a chance to compare how first-timer friends and climbing partners perform on Whitney in all fours seasons, on different routes, and on different itineraries. Overnight trips with camping at Outpost have always been successful and enjoyable.

Another piece of advice: consider splitting your group of 6 into 2-3 semi-independent teams on a summit day, unless you already have a firm agreement that everyone will stick together. Because smaller teams are inherently faster and more efficient, this strategy will increase the chances of success. Also, there will be less frustration due to differences in pace and frequent delays.


Have a great time!