The Caribbean spans more than 700 islands, and many operate under separate governments with their own rules. Planning each leg carefully keeps the journey smooth. Overlooking one requirement can cost you a day.
Check Entry Requirements for Every Island
Each destination sets its own conditions. Some require a visa, while others ask only for proof of onward travel. Many also require digital arrival forms, often submitted days before you land. Keep your passport valid for at least six months, and carry printed copies of all confirmations.
Choose the Right Transport
Ferries connect nearby islands affordably, such as St. Kitts and Nevis. For longer distances, regional airlines are usually the better option. InterCaribbean Airways, for example, operates routes across multiple islands, which makes multi-stop itineraries more practical. Weather can still delay or cancel services, so allow buffer days.
Know the Airline and Baggage Rules
Understanding key operational policies, such as strict weight limits and connection guidelines, covers the most important things to know when flying regional island routes. Baggage allowances are often noticeably smaller than on long-haul international flights due to the limited capacity of smaller aircraft. Furthermore, when separate tickets are booked across different carriers, each airline handles check-in independently; a delay on an initial leg will not protect a missed connection on the next. Allowing at least three hours between flights provides a safe, stress-free buffer.
Plan for Currency and Connectivity
Currencies differ from island to island. You will encounter Eastern Caribbean dollars, US dollars, and euros on the French islands. Carry small bills for taxis and local markets. Check your roaming charges before departure, or buy a regional eSIM to keep your maps and bookings accessible.