As a main result of this paper we give conditions under which the generalized $X$-join of Cayley graphs is a Cayley graph. In particular, we show that $X$-join of isomorphic Cayley graphs is a Cayley grpah. To do this, new properties for a generalized wreath product of permutation groups are given in the case where the base group acts regularly. These are used to give conditions for the generalized wreath product to contain a regular subgroup, which are then applied to generalized $X$-joins of Cayley graphs. Along the way, it is shown that the generalized $X$-join of isomorphic Cayley graphs will always be a vertex transitive graph.