Key West - December
#2
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We went for New Year's Eve several years ago. For weather history, check weatherunderground.com and you'll find that temps can vary from the 50s to the 80s. Something else to consider is the spiking prices of accommodations during special event times like New Year's Eve. Prices can double or sometimes even triple.
#3
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Although the temps can be low it's more frequently pleasant in day and evening. I was there last December (second week) and it was low 80's daytime and high 60's at night - beautiful. I was there the year before in early February and it was about 5 degrees cooler but still nice. It's a very laid back and casual town with a lively but not overwhelming bar secene and plenty of fun clubs, live music and decent restaurants. If you're looking for an upscale trendy scene like South Beach with all the BP, velvet ropes and all night dance clubs it's not the place. If you prefer a place where you can hear some live music, wander from bar to bar with your drink in a plastic cup and relax withfriends... it's a ood choice. I'm not a partier but it strikes me as a place that would be great fun for New Year's Eve, especially with a group. Reserve now!
#4
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I loved Key West! I think it would be a fun and somewhat rowdy New Years but dress would be more casual and a less formal atmosphere. I think the whole spirit of Key West would fit very nicely. I would wear something funky, trendy yet comfortable. No evening gowns. Have a blast and yes book now. Try to book somewhere near Duval Street that is where the action will be and I am sure walking to your party spots would be the best idea.