Go to the farthest island first, then work your way back.

Go to the farthest island first.

That way you avoid backtracking, catch the best ferry schedules, and hit the most popular spot before the crowds arrive. Starting close and hopping outward means you’ll spend your last day rushing back to catch a ferry, and nobody wants that.

If you’re doing a three-island loop (like the Greek Cyclades or Hawaii’s Big Island-Maui-Oahu), fly or ferry to the farthest destination first, then island-hop home. It feels more efficient, and you end the trip relaxed instead of stressed about connections.

You’ll thank yourself when you’re sipping a drink on the last island instead of staring at a departure board.