While shopping or entering any type of business? Yes.
At a restaurant while eating or drinking? Yes to enter. Yes while speaking with the server. No, if seated at a table and eating or drinking. Yes if moving about the restaurant.
Alone in a personal car? No.
In a taxi or Uber? Yes.
At a salon? Yes to enter. No if you are seated and the mask interferes with the service.
While walking around Key West? Yes.
While walking around outside in other municipalities or unincorporated areas of Monroe County? No, unless within six feet of another person. (However, citizens must be able to readily produce a mask, i.e., have it in a pocket or purse.)
While at the beach? Yes, if in Key West. No in the rest of the county unless within 6 feet of someone not in a family group or quarantine circle.