We report the fabrication of multi-island single-electron devices made by lithographic contacting of self-assembled alkanethiol-coated gold nanocrystals. The advantages of this method, which bridges the dimensional gap between lithographic and NC sizes, are (1) that all tunnel junctions are defined by self-assembly rather than lithography and (2) that the ratio of gate capacitance to total capacitance is high. The rich electronic behavior of a double-island device, measured at 4.2 K, is predicted in detail by combining finite element and Monte Carlo simulations with the standard theory of Coulomb blockade with very few adjustable parameters.