Hi Heather,
Thank you for asking a great question! My family went on this fantastic Pirate voyage back in June. We had to meet at the Contemporary Resort. If you are depending on Disney's complimentary transportation, I would suggest that you take the bus to the Magic Kingdom and walk to the Contemporary Resort (10-15 minute walk). Now this all depends on where you are staying on property. If you are staying at the Polynesian or Grand Floridian, just catch the Monorail to the Contemporary Resort.
It's really hard to give you exact information on the weather. We are talking about Florida. I've visited several times around December and each time it was different. It ranged from cold (burrr) to very warm. I would suggest that you keep an eye on weather.com during December so you can get a feel for the weather. I hope this helps!
Have a magical day!
Ca'Sandra
Visit Walt Disney World Resort to explore the magic.
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