We describe our experience with designing and running a matching market for the Israeli "Mechinot" gap-year programs. The main conceptual challenge in the design of this market was the rich set of diversity considerations, which necessitated the development of an appropriate preference-specification language along with corresponding choice-function semantics, which we also theoretically analyze. Our contribution extends the existing toolbox for two-sided matching with soft constraints. This market was run for the first time in January 2018 and matched 1,607 candidates (out of a total of 3,120 candidates) to 35 different programs, has been run twice more since, and has been adopted by the Joint Council of the "Mechinot" gap-year programs for the foreseeable future.