Habana

When: April 2003, April 2004, nearly 2 weeks each time.
Why: workshops organized at the Universidad de la Habana.
If someone were to ask me where to go for a vacation in the next year, Havana would be one of my top answers. Or at least somewhere nearby, cause there are no beaches right in the city, even though it's on the water. At the time that I visited, there were fantastic live bands all over the place in the old town. I could spend all evening at the restaurants and cafes there, enjoying the music and a mojito (and to much lesser extent, the food). Overall, the atmosphere, people, 50's cars, architecture are unique.
Some major hotels have swimming pools (and if you're not staying there its not too hard to sneak in). If you really need to be on the beach, the Playas del Este are about a half hour's drive away. There are places to stay there, and the beaches are clean and empty.