Trinidad - beautiful city and the most Caribbean-like in Cuba
Santa Clara - You can say this is where the Cuban Revolution was finally realized
Santa Clara was the site of the last battle in the Cuban Revolution in late 1958. There were two guerrilla columns that attacked the city, one led by Ernesto Che Guevara and the other led by Camilo Cienfuegos.
There is a museum dedicated to Che Guevara and he's buried in Santa Clara.