Venture, CA to San Diego, CA is almost 200 miles? This is not even remotely realistic with the recumbent pictured. Too heavy and too far and no recumbent experience or conditioning. I would not try it without a broken elbow.

Can't he just ride in the SAG vehicle? Assuming you mean they need a chaperone as he cannot "protect" them. Maybe we are missing something here. How old are the kids, what are they riding, duration of trip, daily mileage, elevation profile of route, etc? What is a multi-weekend trip; did you mean week?