Are regional flights expensive?

Yes. Expect to pay $150-$250 for a 30-minute flight. Book these at least 3 weeks in advance.

Can I island-hop by sailboat?

Yes, it is often more efficient than flying in the Grenadines or BVI. Look for 'bareboat' rentals or 'cabin charters' if you aren't an experienced sailor.

How to plan a Caribbean island-hopping itinerary

Stick to one island chain, like the Grenadines or the Virgin Islands, to minimize time spent in airports. Use a mix of regional puddle-jumpers and local ferries, and never schedule a flight connection with less than three hours of buffer time.

Pick a single geographic cluster. Don't try to go from Jamaica to Barbados. Stick to a cluster like the BVI/USVI, the Grenadines, or the Bahamas. This keeps flights under 45 minutes and costs under $200 per leg.
Book your 'anchor' flights first. Book your international arrival into a major hub (like St. Maarten or St. Lucia) and your departure from another if possible. Use 'multi-city' flight search tools to avoid backtracking.
Use local ferries for short distances. For distances under 20 miles, like between Tortola and Jost Van Dyke, use local ferries. They are cheaper ($30-$60), more reliable than small regional airlines, and offer better views.
Factor in the 'Island Time' buffer. Regional airlines (like interCaribbean or SVG Air) are frequently delayed. Never book a tight connection. If your flight arrives at 2 PM, don't schedule a departing flight before 5 PM.

Are regional flights expensive?: Yes. Expect to pay $150-$250 for a 30-minute flight. Book these at least 3 weeks in advance.
Can I island-hop by sailboat?: Yes, it is often more efficient than flying in the Grenadines or BVI. Look for 'bareboat' rentals or 'cabin charters' if you aren't an experienced sailor.