On my first trip to Havana I got off the bus at the same time as two guys. As usual, I had my Nikon D3000 around my neck. One of them, Raul, spotted a sign for a photography class and asked if I was the teacher. I wasn't, but I took a picture of him and his friend, we talked for a while, and he asked me out. I wound up going back four times in two years. Oh, and we got married.
I still make trips back to Havana with Raul—and my camera. With its mashup of architectural styles and magical Caribbean light, it's my favorite city to photograph. From the top of the Gómez Vila Building, you can shoot most of the bay. Another favorite spot is the seaside road of Malecón because the locals will pose for you; they aren't shy. I'd suggest meeting one.