Is it cheaper to fly or take the ferry?

Ferries are almost always cheaper for distances under 50 miles, but they are subject to sea conditions. Always check the weather forecast before booking a ferry ticket.

Do I need to book regional flights in advance?

Yes. Small planes often have fewer than 20 seats and sell out weeks in advance during high season.

How to plan an efficient Caribbean island-hopping route

Focus on island clusters within the same archipelagos to minimize flight time and costs. Stick to either the Leeward or Windward chains to leverage regional ferry systems and short-haul puddle jumpers rather than hub-and-spoke flying.

Pick one geopolitical cluster. Don't try to cross the entire Caribbean. Stay within the British Virgin Islands/USVI, the French West Indies (St. Barts, St. Martin, Guadeloupe), or the Grenadines. This keeps travel times under 45 minutes.
Check regional carrier schedules. Use local airlines like Winair, InterCaribbean, or Silver Airways. Check their hubs; for instance, St. Maarten is a major hub for the northern islands, while Barbados serves the southern chain.
Prioritize ferries for short gaps. Ferries are cheaper and more reliable than flights for distances under 30 miles. Use the ferry between St. Thomas and St. John (20 mins) or St. Martin and Anguilla (25 mins) to save $200+ per leg.
Minimize check-ins. Island hopping involves frequent customs declarations. Book a maximum of three islands for a 10-day trip to avoid spending your entire vacation in airport security lines.

Is it cheaper to fly or take the ferry?: Ferries are almost always cheaper for distances under 50 miles, but they are subject to sea conditions. Always check the weather forecast before booking a ferry ticket.
Do I need to book regional flights in advance?: Yes. Small planes often have fewer than 20 seats and sell out weeks in advance during high season.