A bit of context, I maintain a small laundry list of open source utilities I've built up over time... when I want to try out a new language I just take one of my libraries and convert it into the new language. I've found that generally does a good job of highlighting language shortcomings and specialties (especially since my packages lean heavily on syntactic sugaring) while also giving me an end product I can run up against a nice suite of robust tests.
I might suggest finding a small (like a dozen source files tops) library you like and just converting it into the new language as you'll be forced to deal with more serious problems than a toy project while also potentially producing something useful on the far side.