Since I've been on WHCL hiatus, I've discovered a number of excellent music programs. One especially worthy of mention is Muriel's Treasure, hosted by WFMU radio host, author, and record producer Irwin Chusid. Muriel's Treasure features plenty of classic Calypso, which I've always enjoyed and have often played on RADIOLA! There are also more modern Caribbean styles, such as Soca. It's fun, witty, joyous music and should be all over the airwaves--but so far this is the only true Caribbean program I've found.
Muriel's Treasure is not currently being broadcast, but there is a wealth of material in the archives, which are also available as a podcast.