The Dominican Republic remains the most visited island in the Caribbean, consistently leading the region with over 8.2 million stay-over visitors annually. Its dominance is fueled by a massive inventory of all-inclusive resorts, particularly in the Punta Cana region, and its successful positioning as a diverse destination offering both luxury beaches and rich colonial history in Santo Domingo. Puerto Rico follows as a strong second, attracting over 5.1 million visitors, largely benefited by its status as a U.S. territory, which allows for easy, passport-free travel for American citizens. Jamaica also ranks highly, experiencing a massive surge in popularity in 2025 and 2026 due to its vibrant cultural appeal, reggae heritage, and major investments in its cruise ports at Ocho Rios and Falmouth. The Bahamas also sees high numbers, often exceeding 3.8 million, though a significant portion of its traffic comes from short-stay cruise passengers arriving from Florida. These "Big Four" islands account for the vast majority of Caribbean tourism, utilizing their large-scale infrastructure and international flight connectivity to maintain a significant lead over smaller boutique islands like Aruba or Barbados.