Is it cheaper to fly or take the ferry?

Ferries are generally cheaper for short distances (under 30 miles), while regional flights are necessary for longer distances. Ferries are also less prone to 'weather cancellations' than small planes.

Can I island hop without pre-booking?

Not recommended. Smaller islands have limited accommodations and flight seats. You risk being stranded for 24+ hours if a flight sells out.

How to plan a 2-week Caribbean island hopping route

Focus on a single geographic chain like the Grenadines or the Virgin Islands to minimize travel time and costs. Dedicate 3-4 days per island and use regional ferries or small puddle-jumper flights rather than trying to cross the entire Caribbean sea.

Select a cluster. Pick one sub-region. Options include the US/British Virgin Islands, the Grenadines, or the Leeward Islands. Do not try to fly from Jamaica to Barbados; the connections are expensive and time-consuming.
Map your flight connections. Check which islands have major international airports (e.g., St. Maarten, Barbados, or Antigua). Start and end your trip at these hubs, then use local carriers like LIAT or InterCaribbean, or inter-island ferries for the legs in between.
Book inter-island transport early. Regional flights often use 19-seater planes that sell out weeks in advance. Book these segments immediately after your main international flight is confirmed.
Account for 'Island Time'. Budget a 'buffer' of at least 4 hours between connecting regional flights. Delays are standard. Never book a tight connection on a different airline ticket.

Is it cheaper to fly or take the ferry?: Ferries are generally cheaper for short distances (under 30 miles), while regional flights are necessary for longer distances. Ferries are also less prone to 'weather cancellations' than small planes.
Can I island hop without pre-booking?: Not recommended. Smaller islands have limited accommodations and flight seats. You risk being stranded for 24+ hours if a flight sells out.