Should I book inter-island flights in advance?

Yes. Regional flights are often on small propeller planes with limited seats and get significantly more expensive as the date approaches.

Is it easy to get around once I land?

It varies. Taxis are common but expensive. Renting a car is better for exploration, but be prepared for steep, winding roads and driving on the left on many islands.

Planning a Two-Week Lesser Antilles Island-Hopping Trip

Stick to a maximum of three islands to avoid spending your entire trip in airports. Focus on the Leeward or Windward groups to leverage reliable ferry connections and regional flights.

Pick a geographic cluster. Don't try to cover the whole chain. Pick the Leeward Islands (e.g., St. Maarten, St. Barts, Anguilla) or the Windward Islands (e.g., St. Lucia, St. Vincent, Grenada) to minimize transit time.
Book your 'Open-Jaw' flights. Fly into the northernmost island of your chosen cluster and out of the southernmost to avoid doubling back. Use major hubs like St. Maarten (SXM) or Barbados (BGI) for international arrivals.
Select your transit method. For islands under 30 miles apart, use local ferries (like the L'Express des Iles). For longer distances, book LIAT or Caribbean Airlines. Book regional flights 60 days in advance to save 30%.
Map your 4-5 day cadence. Allocate 4-5 nights per island. This gives you one day for arrival/acclimation, two full days for exploration, and one day for transit.

Should I book inter-island flights in advance?: Yes. Regional flights are often on small propeller planes with limited seats and get significantly more expensive as the date approaches.
Is it easy to get around once I land?: It varies. Taxis are common but expensive. Renting a car is better for exploration, but be prepared for steep, winding roads and driving on the left on many islands.