The major islands of the Caribbean include: Some of the largest cities in the Caribbean islands include: Santo Domingo, Havana, Santiago de los Caballeros, Port-au-Prince, Kingston, Santiago de Cuba, San Juan, and Holguin.The Caribbean has a number of unique holiday destinations.ome of the largest cities in the Caribbean islands include: Santo Domingo, Havana, Santiago de los Caballeros, Port-au-Prince, Kingston, Santiago de Cuba, San Juan, and Holguin.