The only way you could achieve this is by replacing the first pedestal with a true outdoor rated sub panel. This panel would have a pair of breakers for the first pedestals outlets and then a pair of breakers feeding/protecting the wiring to the second pedal.
If both set of outlets were pulling large amount of amps, they could easily overload the upstream wiring, but that would be protected by the upstream breaker. You could also wire in a third pair of breaker at that fir location to act as a "main" for the 2 sets of outlets so in case of a trip, hopefully you won't have to walk all the way back to the main breaker panel (where ever that is) and reset that breaker.
This might sound complicated but it really is not. Just remember a breaker protects the downstream wiring. The only place "daisy chaining" is allowed is on 120V 15a or 20A circuits.