Southwest Florida's rainy season runs June through September, delivering an afternoon downpour most days, and hurricane season stretches past it into November. Naples knows this isn't theoretical: the region has taken hard hits from Gulf storms in recent memory, and the chimney is the tallest, most exposed thing on nearly every house that has one. Sustained tropical wind pries at caps and chase covers, drives rain horizontally into joints that vertical rain never tests, and flexes flashing until it lifts.
Leaks that start at the chimney rarely announce themselves there. A stain on the ceiling a few feet away, a bubbling patch of paint, a musty note in a guest room nobody uses until the in-laws arrive. That's how chimney water shows up in Naples. Real chimney leak repair starts with finding the true entry point (crown, cap, chase top, flashing, or saturated masonry), because caulking the wrong suspect just reroutes the water somewhere you'll meet it later.
After a storm passes near Collier County, look at the chimney from the ground. A shifted cap, missing cover, fresh stain, or visibly bent component is a reason to request a service visit and avoid using the fireplace until the concern has been evaluated.