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There's no bad time to visit St. Augustine; even on the hottest summer days, the Oldest City's prime position near the Atlantic Ocean makes it easy to cool off with a quick swim. However, any native Floridian will tell you that summer is peak tourist season, so your best bet is to avoid the throngs of visitors that crowd the small city between June and August.
I personally love to visit St. Augustine around the holiday season. The mild winter is manageable, so walking around the cobblestone streets is still quite pleasant as long as you dress appropriately. Keep in mind that the humidity that makes heat stick to your skin in the summer doesn't go away during the winter, so be sure to pack enough layers — Florida winters can pack a surprising chill, even if they only last for a few weeks. The entire city twinkles during the annual Nights of Lights, a magical time of year when thousands of white bulbs light up the sidewalks, trees and buildings. Spring and autumn are equally romantic times to picnic on the lawn of the Castillo de San Marcos fort, stroll along St. George Street and explore the numerous state parks found along the coast.