The use of Application-Specific Instruction-set Processors (ASIP) in embedded systems is a solution to the problem of increasing complexity in the functions these systems have to implement. Architectures based on Very Long Instruction Word (VLIW) have found fertile ground in multimedia electronic appliances thanks to their ability to exploit high degrees of Instruction Level Parallelism (ILP) with a reasonable trade-off in complexity and silicon costs. In this case the ASIP specialization involves a complex interaction between hardware- and software-related issues. In this paper we propose tools and methodologies to cope efficiently with this complexity from a multi-objective perspective. We present EPIC-Explorer, an open platform for estimation and system-level exploration of an EPIC/VLIW architecture. We first analyze the possible design objectives, showing that it is necessary, given the fundamental role played by the VLIW compiler in instruction scheduling, to evaluate the appropriateness of ILP-oriented compilation on a case-by-case basis. Then, in the architecture exploration phase, we will use a multi-objective genetic approach to obtain a set of Pareto-optimal configurations. Finally, by clustering the configurations thus obtained, we extract those representing possible trade-offs between the objectives, which are used as a starting point for evaluation via more accurate estimation models at a subsequent stage in the design flow.