Should I use the ferry or fly?

For a luxury trip, always fly. Ferries are public, crowded, and frequently delayed. Private charters offer a seamless experience from tarmac to transport.

How do I handle currency?

The US Dollar is widely accepted across most luxury Caribbean destinations. Keep a stash of small denominations for tips, but use credit cards for all major bookings.

How to plan a luxury island-hopping trip in the Caribbean

To island-hop luxury-style, focus on using private charter flights between major hubs like St. Barts, Anguilla, and Mustique rather than relying on commercial inter-island ferries. Stick to a maximum of three islands over 10 days to avoid spending your entire vacation in transit and customs.

Choose your cluster. Don't try to cover the whole Caribbean. Pick a cluster: The Northern Leewards (St. Barts, Anguilla, St. Kitts) or The Grenadines (Mustique, Canouan, St. Vincent). This keeps private flight times under 30 minutes.
Secure private transfers. Book Tradewind Aviation or similar regional charter services. They handle private lounge access and expedited customs, which is the only way to make island-hopping feel luxurious rather than exhausting.
Coordinate villa and resort logistics. Arrange for your resort’s concierge to handle port-to-door transfers. In the Caribbean, your luxury begins when you land; never handle your own luggage in a taxi line.
Schedule 'cushion' days. Do not book a flight out of the region on the same day you leave your final island. Weather patterns can ground small aircraft; stay the final night near your major international departure hub (like St. Maarten or Barbados).

Should I use the ferry or fly?: For a luxury trip, always fly. Ferries are public, crowded, and frequently delayed. Private charters offer a seamless experience from tarmac to transport.
How do I handle currency?: The US Dollar is widely accepted across most luxury Caribbean destinations. Keep a stash of small denominations for tips, but use credit cards for all major bookings.