Entanglement is a key feature of many-body quantum systems. Measuring the entropy of different partitions of a quantum system provides a way to probe its entanglement structure. Here, we present and experimentally demonstrate a protocol for measuring the second-order Renyi entropy based on statistical correlations between randomized measurements. Our experiments, carried out with a trapped-ion quantum simulator with partition sizes of up to 10 qubits, prove the overall coherent character of the system dynamics and reveal the growth of entanglement between its parts, in both the absence and presence of disorder. Our protocol represents a universal tool for probing and characterizing engineered quantum systems in the laboratory, which is applicable to arbitrary quantum states of up to several tens of qubits.