Yep.
My sister in Panama City Beach went to bed with a #1 (predicted), but she woke up with a #5 (Michael). She had just moved to Florida 2 months prior. Fortunately, they built their new house and made sure it exceeded current hurricane codes so they just had a few shingles ripped off. But the whole city was traumatized for months/years.
A few years ago a hurricane (I forget which one) was headed north towards Miami and predicted to tear up the East coast of Florida. Many locals evacuated to the West coast of Florida, but overnight the hurricane shifted west and ripped up the West Coast and smacked Tampa, where most of my friends wound up. I stayed home and enjoyed the summer breezes.
If I were to evacuate, I would take the plane North out of Florida, but I have a fairly new T that is theoretically "hurricane resistant". We were fine during Matthew, but the local FBO main hangar was trashed.