Wear Your Mask. Please. No, Not on Your Chin.

KEY WEST, Fla. — Rachel Kobylas longs for the days when her job as a code enforcement officer in the laid-back Florida town of Key West meant that she drove around making sure people turned off noisy power tools after 7 p.m.

She went after overgrown grass, unpermitted construction and boats illegally parked on the street. That all changed this summer, when her main challenge became convincing the tourists, bartenders, T-shirt shop sales clerks and fishermen who flock along Key West’s sweltering streets in shorts and flip-flops that they should also be wearing a mask.

And not just on their chin.

“There have been some really negative interactions,” said Ms. Kobylas, 35, describing the “series of expletives” she routinely confronts, particularly on social media, when she tries to enforce the city’s mask ordinance. “We do our best to be firm but fair and respectful.”

Key West, a city of about 25,000 on the southernmost edge of the continental United States, managed to hold off the coronavirus for several months after the county put checkpoints on the only road into town, keeping visitors out.

Since the road reopened on June 1, infections have leaped twelvefold. The rest of Florida has been gripped by the coronavirus, with more than 461,000 cases and over 6,500 deaths. Thursday was the third day in a row that Florida broke its record for the most deaths reported in a single day.

Yet the experience in Key West, which had made a living off providing a place to escape the world’s troubles, shows that while adopting state and local mask regulations may be politically difficult, making sure they are obeyed can be just as hard.

More than 30 states and an even larger number of cities have enacted a hodgepodge of mask ordinances and executive orders, but many municipalities are barely enforcing them.

Several sheriffs in Colorado and New Mexico have openly defied local rules and publicly refused to carry them out. In California, some city officials publicly warned of harsh penalties but now acknowledge that no one has been ticketed.

A spokesman for the Boston Police Department stressed that it was not enforcing mask rules because Massachusetts has no law requiring masks, which is true. He did not respond when asked about the order the governor issued in May that provided for a $300 fine for not wearing masks in stores, on mass transit and in taxis.

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In a summer that has seen enormous protests of people fighting excessive use of force by the police, many law enforcement agencies have been hesitant to take on a politically divisive issue like masks. Code enforcement officers like Ms. Kobylas in Key West often lack law enforcement training, and many have lost their jobs to city cutbacks.

Credit…Mark Hedden for The New York Times

“At a time when the national narrative from the community and activists and others is that we have too much in our wheelhouse, here we go again,” said Art Acevedo, the police chief in Houston, who is the president of the Major Cities Chiefs Association. “Most police departments are being pragmatic. They are not ignoring it; they’re trying their very best to gain voluntary compliance rather than turn to enforcement through citation.”

In some cities, police chiefs have urged code enforcement divisions to take the lead, Mr. Acevedo said. Fire departments are also stepping in to enforce social distancing capacity regulations.

In a recent video meeting of the American Association of Code Enforcement, six of the 60 members present said they were enforcing mask orders, said Barbara Burlingame, the organization’s president.

“To be quite honest, as a code officer, I would rather it be a police officer because of the anger that some people have about the masks,” said Ms. Burlingame, who works in Norman, Okla. “And I would say almost 100 percent of code officers do not have any kind of self-defense training. They don’t have protective equipment if someone gets violent with them.”

Enforcement of social distancing measures and masks is a critical issue in Florida, which does not have a statewide mask mandate.

South Florida, which has suffered the highest case counts, has begun to enforce local mask rules. At least 140 people have been ticketed in Miami. In Miami Beach, where the penalty is $50, 12 people were cited on the first day the city began cracking down. Another dozen tickets were issued in Fort Lauderdale.

Two hundred miles south in Key West, the city decided it had to tighten the rules as the number of coronavirus cases started to soar. When the roadblock was in place and hotels were closed, Key West had 41 cases. By Thursday, the city had 541 cases.

“The last thing a public official wants to do is legislate common sense,” Mayor Teri Johnston said. “We’ve had brides saying, ‘I’m devastated! I booked my wedding!’ Why would you do that in the middle of a global pandemic when we’re a hot spot?”

Credit…Mark Hedden for The New York Times

The town is now flooded with tourists, some of whom bristle at the idea of being masked on vacation. The city has required masks outdoors since mid-July, even while riding a bicycle or walking alone down an empty street. Couples getting married can briefly take them off for photos. Singers in the bars got an exemption after they complained, but they still have to put up a shield and maintain 10 feet of distance from their audience, which is impossible at many venues.

“Ninety percent of the people are wearing their masks, just not over their nose and mouths,” said Jim Young, Key West’s director of code enforcement.

He and Ms. Kobylas let smokers and people with a beverage in their hands slide, since partaking while wearing a mask could be problematic. Violators who had previously been warned get slapped with a $250 citation. The city has levied more than $13,000 in fines. Three people have been arrested.

The city has tried to go easy on tourists — nearly 80 percent of tickets it has issued went to local residents — but it has little patience for the workers who serve them. Code enforcers issued $1,500 in fines to a single restaurant when they found most of the cooks in the kitchen without masks. A 17-year-old earning $9 an hour at an ice cream parlor was fined because a co-worker had previously been warned.

“To businesses that are really struggling to keep the doors open, $250 is not nothing,” said Amanda Velázquez, the owner of the ice cream shop where the teenager was cited. “We see tourists up and down the street all day long without masks on. I don’t think that’s fair.”

In an encounter that underscored the difficulty of enforcing such a contentious issue in the midst of a civil rights movement, a man who was arrested on July 3 immediately accused the code enforcement officers of targeting him because he was Hispanic.

That mask enforcement effort, led by Mr. Young, the code enforcement director, ended with Mr. Young’s hands across the young man’s throat, according to body camera footage.

“We were waiting for the police, so I was just trying to get this guy to calm down,” Mr. Young said. “He just went off.”

Code officers said the tourist in that case, Joshua Gomez, a 25-year-old from Sebring, Fla., had been warned previously and was spotted a second time in a restaurant without his mask properly on his face. The video shows him with his mask back on — with his nose showing at times — while he refused to turn over his driver’s license. He walked out with his hands up in the air as he repeated: “You’re not touching me. I’m not touching you.”

Credit…City of Key West

Mr. Young, who had called the police, pushed his body against Mr. Gomez and tried to block his exit. Mr. Gomez wrestled away, and Mr. Young, a former police officer, briefly pinned him against a post by his neck, according to the video; with Ms. Kobylas’s help, he held him until the police arrived while Mr. Gomez hurled a collection of invectives.

Mr. Gomez, whose lawyer declined to comment, was arrested and accused of disorderly conduct and two counts of felony battery after the code enforcement director said he had been “chest bumped.”

As the police officers were debating what to cite him with, Officer Michael Andruzzi, whose comments were captured on the Police Department’s footage, made the case for tough charges. “Make a point,” he said. “This is what the city wants, this is what the city gets.”

Contributing reporting were Jack Healy from Denver, Simon Romero in Albuquerque, Jennifer Medina from Los Angeles and Sarah Mervosh from New York.