Multi-island itinerary circuits for five archipelagos — the recommended island sequence, ferry vs. flight legs, minimum time per stop, best season, and the transport mistake that costs most travelers a day. Covers the Greek Cyclades, Thailand's Gulf islands, the Philippines, the Azores, and the Canary Islands. For individual island picks rather than a multi-stop route, see Best Islands.
Ferries are usually cheaper and let you watch the crossing. Flights are the only option once islands aren't on the same ferry network, and worth it past about three hours by boat.
A one-night island stop spends half its time on transfers. Stacking three or more one-night stays is the itinerary that never lands anywhere long enough to enjoy it.
Inter-island ferry frequency — and cancellation risk from wind or swell — swings by season far more than the islands' own climate does. Check the schedule, not just the forecast.
A delayed ferry or small regional flight on the last inter-island leg is common. One buffer night before any onward or return flight is the cheapest insurance on the trip.
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