Caribbean Complete Guide 2026: Jamaica, Dominican Republic, Bahamas, Puerto Rico, St Lucia and Beyond
Browse more guides: Caribbean (multi-nation) travel | North America / Americas / Caribbean destinations Caribbean Complete Guide 2026: Jamaica, Dominican Republic, Bahamas, Puerto Rico, St Lucia and Beyond TL;DR I planned my first Caribbean trip thinking it was one destination. I was wrong. The Caribbean is 28 nations and over 700 islands scattered across roughly 2.75 million square kilometers of sea, and each island carries its own language, currency, food, music, and visa rules. I spent three weeks island hopping across five countries on my last trip, and I still felt like I had barely started. For first-time visitors I recommend anchoring the trip in two or three islands rather than rushing through six. Jamaica gives me reggae heritage, Blue Mountains coffee, and Dunn's River Falls. The Dominican Republic gives me all-inclusive Punta Cana resorts plus Santo Domingo's Zona Colonial, which UNESCO inscribed in 1990 as the first permanent Spanish settlement in the Americas...