
A rideshare operation will continue — and expand — in Islamorada, following the council’s unanimous support of a new agreement with Freebee.
Approval by the council during a June 11 meeting will allow Freebee to operate three vehicles all at once, while offering new, longer hours beginning July 1 throughout the village and portions of Tavernier. Three vehicles will transport visitors and locals to and from restaurants, shops, hotels and other destinations seven days a week from 7 a.m. to midnight.
Under a prior agreement, Freebee’s transportation service was staggered, with the first vehicle running from 7 a.m. to 5 p.m., the second vehicle operating from noon to 10 p.m. and the third vehicle running between 2 p.m. and midnight.
A rideshare expansion through Freebee is partially funded by a Florida Department of Transportation grant, which council members also approved on June 11. While annual costs for the Freebee program will increase from $342,504 to $553,330, a grant from FDOT — which funds half the expense — will reduce the village’s costs by $65,839.
The council initially approved a six-month trial run with Freebee in November 2018. The initial program saw Freebee using golf carts to transport locals and guests on Upper Matecumbe Key. By July 2019, the village agreed to expand the service villagewide by using two vans and a golf cart.
In 2021, service expanded beyond Tavernier Creek Bridge to places including Tavernier Towne Center, Good Health Clinic and Mariners Hospital in Tavernier. The golf cart servicing riders on Upper Matcumbe Key was replaced by a Tesla X.
Eventually, the village’s cost for Freebee could go to zero with Monroe County seeking to bring a uniform transportation service to the islands in the near future. In mid-May, the county commission approved an agreement with Freebee for transportation services to the Lower Keys. Five vehicles will run locals and guests in and around the Southernmost City and the neighboring Stock Island seven days a week from 5 a.m. to 9 p.m. The county, too, received a FDOT grant to fund 50% of the expense.
“Frankly, they put a better proposal together than anybody,” Richard Clark, the county transportation director told council members at a May 7 meeting. “There’s a really good chance we’re in the same place as you guys are up here.”
Islamorada council members initially pumped the brakes on a Freebee expansion and sought public input on the service’s effectiveness. Eventually, the council agreed to send the service out to bid and form an evaluation committee composed of area leaders and residents to rate service providers interested in transporting people in Islamorada.
The committee’s selection of Circuit over Freebee, however, was deemed “fatally flawed” by then-interim manager Kimberly Matthews. Formation of a new committee was expected to consider and review a new set of proposals. The group was never convened, leading councilman Henry Rosenthal to question why.
“I believe we should form that second committee. I don’t know how it was flawed. No one took the time or had the guts to tell us what the flaw was,” Rosenthal said.
Islamorada Vice Mayor Mahoney, who spearheaded the effort to evaluate Freebee’s service, was a member of the evaluation committee. Mahoney told fellow council members the group wasn’t given the right rules by staff.
“After they (the committee) voted and were told the correct way to do things, they re-voted. That’s what made it illegal; they’re not allowed to re-vote,” Mahoney said.
Despite all the work to evaluate rideshare in the village, Mahoney acknowledged transportation services should be turned over to Monroe County.
“We have no business in transportation and no business in wastewater. I’m sorry, we’re not big enough to be dabbling in those two things,” Mahoney said.

Breakwater restoration
In other news, council members chose Tavernier-based Adventure Environmental to conduct a $1.8 million breakwater restoration project at Founders Park. Constructed in the 1960s, the breakwater protects park marina infrastructure and vessels from flooding and wave events. It’s weathered two major storms, Hurricane Wilma in 2005 and Hurricane Irma in 2017.
Ten companies sent proposals to the village. A three-person evaluation committee ranked Earth Tech Enterprises as the top firm to conduct the work. Peter Frezza, environmental resources manager, said Earth Tech, based out of Fort Myers, performed several jobs in Monroe County, including stabilization repair work at the West Martello jetty in Key West.
“Earth Tech is extremely qualified. I’ve never seen such congruence in the committee’s evaluation scoring,” Frezza said.
Council members elected to go with the local company, however, in Adventure Environmental.
“I want to look at people who’ve done a lot of work in this county for years. Adventure did tens of millions of work for Monroe County after Irma,” Mayor Buddy Pinder said.
Costs for the breakwater restoration are covered through a Resilient Florida grant administered by the Department of Environmental Protection.
Founders Park master plan

Council members unanimously approved a resolution selecting the park-planning firm Miller Legg to create a master plan at Founders Park. In March, the village solicited proposals to evaluate facilities and elements of the park. By conducting public meetings, the firm will eventually provide a draft master plan presenting various alternatives for council’s review.
Maria Bagiotti, park director, said the village received four proposals from firms. An evaluation committee ranked Miller Legg as No. 1.
“All firms were qualified but we really felt Miller Legg had the best approach to the plan,” she said. “They had a lot of similar projects and the qualifications were high. They had experience in master plans throughout the whole state of Florida.”
Before the council’s approval, councilwoman Elizabeth Jolin wanted to get the thoughts from Miller Legg representatives regarding the growing popularity of pickleball. At Founders, the three courts in the dedicated pickleball area are always busy. Two more have been added to the basketball courts, but players say it’s not enough.
“It’s been discussed many times with the Parks and Recreation Advisory Committee. There’s a pretty big request for that,” Bagiotti said.
Mike Kroll, president of Miller Legg, said pickleball is a growing trend. He said there are two approaches to pickleball. One is through multipurpose courts for pickleball and other sports. The other is a standalone facility for pickleball players.
“There really needs to be a balance that allows us to facilitate regular play while also accommodating other court sports,” Kroll said.