3 country guides
Cuba is the largest Caribbean island, with colonial cities, tobacco valleys, long beaches and live music that runs every night in the main towns. Staying in casas particulares — licensed family homes — is the normal and most useful way to travel. Shortages and limited card acceptance mean planning cash and supplies in advance.
The Dominican Republic is better known for all-inclusive resorts than for the mountains, waterfalls and whale bay that make up its interior and north coast. It has the Caribbean's highest peak and its oldest colonial city. Independent travel is straightforward and much cheaper than the resort strips suggest.
Jamaica has a mountainous interior of rivers, waterfalls and coffee slopes behind its resort coastline, and a music history that is genuinely central to the culture. Distances look small but mountain roads are slow. The north coast holds most resorts; Port Antonio and the Blue Mountains are the quieter alternatives.