Re: Best time of year to travel to Florida Keys Dan...You can't lose in terms of enjoyment by any of your choices....
The Keys and Disney (WDW) could not be any more different and diverse however and about 6 hours separate the two also depending where in the Keys you plan to go.
The "top" of the Florida Keys are 60-90 minutes south of Miami and can easily be reached in a car (there is limited or no real public transport). You can get a flavor of the Keys by staying in Key Largo between mile markers (MM) 104 and 94 (try to Marina del Mar--a diving resort about MM 96 or 98) but as you drive further south, the waters and views get nicer and the pace much slower until you reach Key West at MM 0. Key West is a whole another world.....but probably not best experienced with kids--although I NEVER turn down a chance at Key West.
I would avoid the Keys during holiday periods or major Festivals (like Fantasy Fest) due to crowds & prices--although in this economy--there are some deals to be had. The best time for the Keys is late spring or late fall for best water conditions if you plan to snorkel/dive and to avoid or minimize both the heat/humidity and the hurricane & rainy season (June-Nov but really August-October).
Otherwise, the Keys are great year-round. One downside if you drive from Miami to Key West (about 160 miles and 3-4 hrs or so).. is that you are then about 6-8 hours from WDW up north in Central FL. and that is without a stop in the Everglades for the requisite Airboat rides to see the alligators.
WDW is about 3 hrs north of Miami if you take the toll turnpike and about 4-5 hours if you take the free Interstate 95 up the coast..... There are some nice sidetrips off I-95 like the Navy Seal Museum, Kennedy Space Station & NASA, Daytona Beach, etc.
WDW itself can be a week-long adventure if you spend 1 day in each of the 4 major theme parks, and one day in a waterpark.
If you had to pick a time to see WDW, I'd really avoid holiday times and stick to mid-weeks during normal school years to minimize crowds.
Is there something more specific you want or need? I'll try my best to help you out.
TS (in Florida for the time being--lol).
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