By Jim McCarthy, Sara Matthis and Mandy Miles

Servers, retail associates, dockhands, front desk associates — the list of employment opportunities goes on and on in the Florida Keys.

“Now Hiring” signs and Facebook posts seeking job candidates aren’t new to the island chain —  with living costs soaring and burnout among those working more than one job. 

But workforce shortages are becoming so severe that some employers are offering more pay and added benefits. The availability of affordable housing remains a challenge. 

“I think it’s probably our biggest problem for our businesses,” said Judy Hull, executive director of the Islamorada Chamber of Commerce. “Everyone’s looking for workers, but there’s no employee pool.”

The same is true for many businesses at the other end of the island chain in Key West, where it’s not feasible for workers to live in Homestead or Miami and commute to jobs in the Upper Keys. 

“What workers?” asked bar owner and former Key West city commissioner Mark Rossi, who employs about 80 people in various positions at his Rick’s/Durty Harry’s entertainment complex on Duval Street. “You can’t find staff. There’s no one here, and it’s gotten worse since the pandemic started, much, much worse.” 

Job postings in the Upper Keys reached into the hundreds for April. Resorts are seeking everything from front desk associates to maintenance workers, while Starbucks needs baristas and stores like Winn Dixie search for customer service employees. 

Hotels need everything from food and beverage managers to bartenders and front desk attendants. Around 100 restaurant jobs are open in the Upper Keys.  

As of April 13, the employment website showed listings for 663 full-time jobs within 10 miles of Key West. Positions run the gamut from police dispatchers and pool attendants to boat mates, bartenders, art framers, receptionists, front desk agents and lab technicians.

“It’s pretty much across the board,” Hull said. “If you called almost any business from banking, lodging, water sports and insurance, everyone is searching.”

At Key West’s Casa Marina and The Reach resorts, managing director John Trovato and HR director Greer Cornell acknowledged the staffing challenges that followed employee furloughs during the COVID shutdown. As part of the Hilton Worldwide network, Cornell said, the company offers “excellent health benefits” and employee housing based on availability.

“We also have a very aggressive recruiting program underway that includes a signing bonus for new hires and a finder’s fee bonus for team members that refer a new hire – both of which are paid out after 90 days of successful employment,” Cornell said. 

Key Largo Chamber of Commerce president Elizabeth Moscynski relayed similar workforce shortages in Key Largo, especially within the lodging industry, where more than 60 jobs await applicants. Moscynski attributes the workforce crisis in the Keys to several factors. 

“After the COVID exodus last year, many folks left the area and they’re not coming back. The cost of living is too high,” she said. “And some folks are opting to stay on unemployment.”

Robert Goltz took the helm of the Key West Chamber of Commerce this week, and said he is still educating himself about the workforce challenges, “but it’s absolutely on my radar as a top priority.”

Marathon Chamber of Commerce CEO Dan Samess says he doesn’t see unemployment benefits having a big impact on the Keys’ lack of employees; rather, he says, he thinks the workforce has shrunk. 

“I feel like it’s more of a supply issue rather than people sitting at home because they are collecting unemployment,” Samess said. “And I do think we lost some people when COVID-19 hit, especially when we shut down. People went back to the mainland to live with family or friends rather than continue to pay high rents and expenses down here.” 

Samess said he believes that of the workers who did leave, most were younger. 

“Younger people were less in a position to weather this unique storm,” he said. “It’s still eerie. After Hurricane Irma, we could see the destruction; but with the pandemic, the effect on our economy is invisible.”

Johnny Maddox, who has a charter fishing fleet in the Middle Keys, said many captains and mates went back to the mainland at the height of the pandemic shutdown. 

“The ones that are still here are running double duty on a couple of boats,” Maddox said. He said it’s not uncommon to schedule a mate to work, only to have him cancel because “he’s got a better offer down the street.” 

Maddox said he’s going out of his way, literally, to get helpers on the boat, including offering transportation. He said he’s posted many want ads for captains and mates on Facebook and industry websites. One consistent worker spends a week in West Palm and comes down to the Keys the following week. 

“I get five charters back to back and it’s worth his while. Plus, he has friends in town so he can stay with them,” Maddox said. “We are blessed with the amount of business we have right now. I just feel that the struggle to find good help is always going to be there because of the cost of living in the Keys.”

Chris Gratton of Keys Contracting Services said the lack of employees is responsible for the entire company’s pivot over the last two years. And though COVID-19 played a role, the overriding cause is a lack of qualified employees. 

“We’re becoming more and more of a management type company, where we oversee the project and hire the subcontractors from the mainland,” said Gratton. He said the company went from a high of 65 employees to the 20 it has now. He said Keys Contracting Services is steering away from the smaller one- and two-day jobs, such as replacing doors or building a deck, for bigger projects because he just doesn’t have the staff.

“This employee shortage isn’t just in my line of work, it’s everybody,” Gratton said. “We just returned from a trip and on the drive down the Keys we saw it. Listen, restaurants have always had signs out front looking for wait staff. But now the sign lists hostesses, line cooks, servers, bartenders. This is going to get really tough.” 

Ocean Studies Charter School principal Trisha Woods said it’s often difficult to find teachers, given the cost of housing and availability of a place that’s more than one bedroom and one bathroom. 

Woods said the majority of the teachers are coming back next year. The school in Key Largo is expanding with new sixth grade classes, and the challenge to find two teachers is on. 

“The pandemic hasn’t affected that,” she said. “It’s an ongoing problem because rent is so high.”

Flowers and bouquets fill Maria Estrada’s Upper Matecumbe shop. While she’s out delivering, her husband is usually in the back room preparing flowers. And that’s pretty much it in the way of workers at the moment for Estrada. 

“You can see I have no employees,” she said. “I need someone to work in the flower shop, but I can’t find anyone.”

Dawn Basler, owner of Island Time Day Spa in Tavernier, has been trying to hire a massage therapist for eight weeks now. No applications have come in yet. 

“It’s very frustrating,” she said. “It’s like everyone is on unemployment. Unfortunately, if we don’t find a therapist, our company won’t make it.”


The College of the Florida Keys (CFK) invites the community to join students and alumni seeking employment at its annual job fair on Tuesday, April 20 from noon to 2 p.m. in the courtyard of the Key West Campus. Face masks and social distancing are required at the outdoor event.  

Job seekers are encouraged to come prepared with resumes and “dressed to impress” the wide range of local employers that are looking for qualified candidates to join their organizations.  

The following businesses will be present:
Barbary Beach House
Casa Marina
Centennial Bank
CFK Summer Adventure Camps
Firefly and Tiger Bar
First State Bank
Grace Lutheran School
Guidance Care Center Inc.
Hyatt Centric Key West
Key West Police Department
Monroe County Sheriff’s Office
Ocean Key Resort and Spa
Opal Collection (Opal Key West, Sunset Key, Laureate, Capitana)
Parrot Key Hotel & Villas
Pat Croce & Company Half Shell Raw Bar
Providence Healthcare Services
Senses at Play – Family Affair – Wedding Services
Spottswood Companies
TJ Maxx
Tropical Shells & Gifts 

For more information, contact Laura Weeks, CFK coordinator of student success services, at 305-809-3164 or [email protected]