We spent 4 holiday seasons at HHI, 3 over New Year's and one over Christmas(both 5 nights). It ranged from 30 degrees with gloves and hats to 50-60 degrees with DS swimming in heated pool at the beach house. It is pleasant either way and walking or biking on the beach is fine for Jan, but don't expect sun-bathing or swimming on the beach. FYI, we heard that many of the restaurants and shops close after New Year's for a brief vacation for the islanders(many go skiing!). Don't know the exact timing, but we have stayed as long as Jan 3 and it was fine. HHI resort has so many activites going on for all the seasons! We love ths holidays there as much as WDW..just alot more relaxing.
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