How to plan a multi-island Caribbean trip

Focus on islands within the same regional cluster to minimize travel time and costs. Book your regional flights or ferry connections at least three months in advance, as island-hopping is expensive and rarely flexible.

1. Pick a regional hub. Don't try to cross the entire Caribbean. Choose a cluster like the Virgin Islands (USVI/BVI), the Leeward Islands (St. Maarten/Anguilla/St. Barts), or the Southern Caribbean (Aruba/Bonaire/Curacao). This keeps regional flight times under 60 minutes.
2. Map your transit routes. Check flight availability between islands using small carriers like LIAT, InterCaribbean, or Winair. If staying close, look for high-speed ferry schedules. Never assume a direct route exists just because the islands look close on a map.
3. Sync your arrival and departure. Fly into one major 'gateway' island (like St. Maarten or Barbados) and out of another to save time. Book these as a 'multi-city' ticket on your long-haul airline rather than buying separate one-way tickets.
4. Budget for inter-island taxes. Set aside $100-$150 per person per island hop. These flights are short but carry heavy airport taxes and high demand premiums.

Can I island hop by ferry?

Yes, but only in specific areas. The USVI to BVI, or St. Maarten to Anguilla are easy. Do not expect ferry service between distant island groups.

Are inter-island flights expensive?

Yes. Expect to pay $150-$250 for a 30-minute flight. Book them early as small planes have limited capacity.

Do I need to carry my passport for every flight?

Yes. Every inter-island flight is an international flight with formal customs and immigration.