I have booked a fortnight in Naples in May. I have been to the Southern Florida area on three previous occasions around May and June and have never experienced bad weather. Why then do I keep reading about September to April being the best time to visit this area, as though May onward should be avoided.
Naples in May
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The mid day sun can be blazing and afternoon temperatures can get very hot May to August, but that doesn't mean you can't thoroughly enjoy yourself.
You just need to be more cautious of the sun and heat. That means you don't do full 5-6hr days at the beach.
Florida can be enjoyed 12mo of the year.
Yes, it will be very, very hot. There will be a brief thunderstorm, often quite spectacular, almost every afternoon, after which it may well be very pleasant. Naples itself normally has a sea breeze, but touring the natural areas inland (Big Cypress Swamp, the Everglades) will be a tropical experience.
Air conditioning is universal, and the locals tend to keep it very cold so that it is a shock to go out or in.
Since the season is winter, it will not be crowded, though some places will not be open. But the beaches are spectacular and the city itself, once off highway 41, is lovely. And even US 41 is fascinating because it will be nothing at all like home.
I live in Naples. I understand why they would include November through April. (April is one of my favorite months.) But I'm puzzled about September. Next to July & August, September is ridiculously Hot. Even October can be scorching hot. There have been many Halloweens where I'm sweating while taking my kids trick-or-treating.
May is a good time to visit because the hot weather hasn't peaked yet but you don't have to deal with the crowds because all of the snowbirds have gone home and kids are still in school.