How to Plan an Island-Hopping Holiday

1. Pick the region from your season, not your Pinterest board

Every region has months where hopping simply does not work. The Andaman coast shuts down in the southwest monsoon; the Philippines gets typhoons from September; the Caribbean has a hurricane peak in September and October; the Cyclades close most hotels from November to March.

Start with when you can travel, then choose from the regions that are in season. It is the single decision that prevents the most disappointment.

2. Set the number of islands by nights available

Divide your nights by three and round down. Seven nights means two islands, ten means three, fourteen means four or five if the hops are short. Anything denser produces a trip you remember as tiring.

3. Order the route so you never backtrack

Draw the islands on a line between your arrival and departure airports and travel along it. Where an open-jaw flight is available — into Phuket, out of Krabi; into Bali, out of Lombok — take it. It usually costs little more and saves a full travel day.

Put the least-connected island at the start, while your schedule still has slack, and the best-connected island at the end so a cancellation cannot cost you your flight home.

4. Book in this order

Sequence matters because each booking constrains the next:

• International flights, and any internal flight on a small airstrip — these sell out and rise fastest.
• First and last night accommodation, so arrival and departure are never improvised.
• Middle-island accommodation, refundable where possible.
• Ferries — four to six weeks ahead in peak season, a few days ahead otherwise.
• Day tours and dives — locally, the evening before, once you can see the wind forecast.

5. Build one buffer day per week

Weather cancels boats. A buffer day is not a wasted day — it is an unplanned beach day that becomes a rescue day when the catamaran does not sail. Never schedule the last inter-island crossing on the same day as an international flight.