For timing considerations if were planning a trip, I consider we're about 9 weeks away from Nov. The incubation period for this virus can be up to 2 weeks for symptomatic expression (if symptoms arise). When needed and on average, hospitalization could occur anywhere up to 4 weeks from initial infection. So case count and impact to hospital capacity have a lagging rate from initial infection or onset. These aren't "hard numbers," it's a way to consider why it can take some areas several weeks to come up or down to a stable plateau.
Schools are restarting now, and some schools have delayed to mid-September or even October. I expect spread to some degree once more people, regardless of age, start to congregate again. So I expect numbers to go at least slightly up heading into the fall where schools are in person, and states start to reopen.
These are the factors I think about when considering how long a given area may be in a place of immediate public health risk. 9 weeks seems far too short to have Florida's numbers down to a level that masks won't be required. As others have said, I expect masks to be required through at least 2020, and likely during 2021 until transmission/spread is reliably contained.
Best wishes as you consider your travel plans and what might be best for the health and safety of your family and the families around you.