Florida is an all-party consent state, so it must first be determined whether recording without consent is legal. That then depends on the circumstances surrounding the recording. There is no law against taking silent video of a person in public, but it may not be legal to record another person's oral communication. The fact that a person is a police officer, or is a police officer conducting his business, does not make the wiretapping law universally inapplicable. It does, though, mean that voice recording is legal only when there is no reasonable expectation of privacy. Police orders given at a demonstration are not uttered with an expectation of privacy, but private words uttered between another person and the officer on a public street may not pass the "reasonable expectation of privacy" filter. The importance of this is that if the recording is illegal, wearing a mask to do it is illegal.
Supposing that the wiretapping law was irrelevant, you would not be breaking the law, under a plain reading of the law, except for the potentially subjective elements pertaining to "the intent to intimidate, threaten, abuse, or harass" – let us assume that no other actions could be added to the charge, and the potential arrest rests only on the fact of recording while masked.
This does not mean that the police can't stop you, even if you have an unrecognized right to do this, because a police officer also has qualified immunity, so there may be no consequences for the officer who arrests you (it depends on whether there is a clearly-established constitutional right that is being violated). Fields & Garaci v. Philadelphia, decided a little over a week ago, is an important case changing the law in the 3rd Circuit, as to whether you have a right to record police. The lower court said there is no such right, the higher court disagreed and established such a right:
Simply put, the First Amendment protects the act of
photographing, filming, or otherwise recording police officers
conducting their official duties in public.
The 11th Circuit (which includes Florida), is likewise on board with this position. Smith v. City of Cumming held that there is
a First Amendment right, subject to reasonable time, manner and place
restrictions, to photograph or videotape police conduct. The First
Amendment protects the right to gather information about what public
officials do on public property, and specifically, a right to record
matters of public interest
You are "within your rights" to record in this context, but that right may not be recognized in court (because of limits on what is an established 1st Amendment right, and because of police qualified immunity, where Fields & Garaci lost). The court said
Government actors are entitled to qualified immunity unless
they violated a constitutional right “so clearly established
that ‘every reasonable official would have understood that what
he is doing violates that right.’”
Henceforth, in the 3rd Circuit, police are "on notice", but in this case, they were not, so qualified immunity existed. Since Smith v. Cumming is quite old, there would be no qualified immunity. However.
There is some Circuit-specific variation in the scope of the right. The 3rd Circuit recognizes a right of "otherwise recording police" (which includes voice recording), but the 11th district might be understood as saying that the right covers photographing or videotaping, but not voice recording. The problem is that unless it is so clearly understood that there is a right to voice record, then there is qualified immunity for the police.
Wearing a mask does not change the situation.
