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Chiang Mai, flight: best travel logistics to which Island?

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November 22 of this year....
If I done my research correctly there are three airports that you can jump off to the islands: Samui, Krabi and Phuket. Starting from Chiang Mai. And have five nights to relax before going back to Bangkok for three nights. Then home.

Struggling to BALANCE tranquil beach experience with logistics of getting from Chiang Mai to a island in one day. I discovered Bangkok Air has one non-stop to Samui, where the rest of their flights have one stop as it does to Krabi. And one non-stop to Phuket. All arrive late afternoon. But discovered that Asia Airlines provide flight, land and ferry to the islands. Might be the best option?

1) Concerns are weather conditions at this time of year, are some islands better suited for good weather then others?

2) logistics of getting from the airport to a boat to one of the islands.

Can anyone advise what might be a nice balance of logistics time wise and a island that offers tranquility, along with (my fantasy of a simple cottage with hammock on the beach).

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