Best Caribbean Tours in May

The Caribbean is an archipelago of thousands of islands and cays defined by its mountainous rainforests and volcanic peaks. The region serves as a crossroads of African, European, and Indigenous traditions, creating a cultural landscape where every island has a distinct identity. Iconic cities such as Havana, Old San Juan, Santo Domingo, and Willemstad function as open-air museums. Visitors can explore 16th-century Spanish forts, admire Dutch colonial architecture, or visit the oldest cathedrals in the Americas. Beyond the cities, the geography supports a wide range of activities. In Jamaica, travelers hike the Blue Mountains or climb Dunn’s River Falls, while the volcanic Pitons in Saint Lucia provide a backdrop for sailing. The region is also a global hub for music and festivals.