If you are a citizen of a Visa Waiver Program (VWP) country (such as the UK, Australia, or much of the EU) and your Caribbean cruise departs from or visits a U.S. port (like Miami, San Juan, or St. Thomas), you must obtain an ESTA before you travel. In 2026, this is a non-negotiable requirement for boarding the ship, as the cruise line acts as the "carrier" into U.S. territory. Even for "Closed-Loop" cruises that start and end in the same U.S. port, the ESTA is required to verify your eligibility to enter the United States. If your cruise departs from a non-U.S. port (like Barbados or Martinique) and does not visit any U.S. territories, you may not need an ESTA, but you might instead need an Electronic Travel Authorization (eTA) for Canada or the UK if you are transiting through those countries. Always check your specific itinerary; if "Key West," "Puerto Rico," or "The U.S. Virgin Islands" appear on your schedule, you are legally entering the United States and must have your ESTA approved at least 72 hours before your flight or cruise check-in.