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3 wks during peak season or just 2 wks in Hawaii - How would you split it?

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The company my husband (DH) works for shuts down from Dec 23rd to 27th this year, and we like to use our vacation days strategically to maximize our holidays. If we travel during this break, we use only 2 weeks of vacation time but get 3 weeks off.

I'm wondering whether to travel to Hawaii during Dec 7th to 29th, which seems like very high season, or just going for 2 weeks at some other time of the year?

How much more expensive/crowded will it be during December than say October? I know Hawaii suffered a tourism slump a few years ago but last year had record number of tourists so I guess there aren't any deals during high season, even if we book early?

How would you split your time differently btwn islands if you were going for 2 weeks vs. 3 weeks?

We're coming from Toronto area so flights will be expensive, as well as days used up for travelling.

DH & I are more "independent travellers" than tour group types but will likely do a kayaking day-tour, do a lot of snorkelling on our own, a couple of half-day hikes, and as it's my first visit to Hawaii, we'll take in the usual "tourist must do's". If we stay longer at each locale, I'll try to see what we can find on vrbo.

All suggestions much appreciated - enjoy-la!

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