A couple weeks ago, a slightly inebriated fan asked me, “Yo Chris, what’s up with the Cuba cruise?” Although he may not have been a poet laureate, his words impacted me just the same. It suddenly occurred to me that my hosting a cruise might seem slightly out of left field, so please allow me to explain how it came to be.

So here I am in Washington, D.C. after a solo show at the lovely City Winery. I'm booked at a fancy hotel a half mile from the White House. Had I been aware that the majority of rooms here had windows overlooking a sprawling view of the lobby and not the outdoors, I probably wouldn't have stayed here. However the lobby is kind of pretty, and I realize I am lucky to stay here. When I think back to the early days, staying at the very un-fancy Motel 6's, where the windows overlooked eig...