Most Caribbean cruises in 2026 depart from major "gateway" ports in Florida, with PortMiami, Port Everglades (Fort Lauderdale), and Port Canaveral (Orlando) being the busiest hubs in the world. However, departure options have expanded significantly to serve different regions; you can find frequent sailings from Galveston (Texas), New Orleans, and Tampa for Western Caribbean routes. For those in the Northeast, New York (Manhattan and Brooklyn) and Baltimore offer year-round departures, though these usually involve a few extra sea days. In the Caribbean itself, San Juan (Puerto Rico) and Bridgetown (Barbados) serve as major "homeports" for Southern Caribbean itineraries, allowing travelers to start their vacation deep in the tropics and visit more islands in a shorter timeframe without the long transit from the U.S. mainland.