Islamorada's Freebee Isn't Free Anymore. The Bigger Date Is June 2027.

The first version of Islamorada's ride service couldn't cross a bridge. It started in 2018 as a pilot of golf carts working the downtown stretch of Upper Matecumbe. The carts were popular, but they had to stay on one key. Today the same service runs two Tesla Model Ys and an electric van from 7 a.m. to midnight every day, over the highway bridges between Tavernier and Lower Matecumbe.

Since July 20, each ride also costs $2.

The fare got most of the attention this summer. The date that matters more for anyone who rides Freebee to work, to the clinic or home from dinner is June 2027. That is when the state grant paying half the bill reaches the end of its final round. The $2 fare is the Village's first step toward paying for the service on its own.

Eight Years of Freebee in Islamorada

Freebee grew in steps. Each step made it bigger and more costly to run:

1. 2018. The Village Council approves a pilot for downtown Upper Matecumbe using golf carts, which can't cross bridges.
2. Early 2020. Vans replace the carts, so riders can travel the highway and the bridges from Tavernier to Lower Matecumbe.
3. The state grant years. The Village wins money from the Florida Department of Transportation's Public Transit Service Development Program, which covers 50% of Freebee's cost. To qualify for the last round, the Village had to expand service, so it raised weekly service hours from 210 to 357.
4. November 2024 through October 2025. More than 56,000 riders use the service, according to Village staff as reported by KeysNews.
5. June 11, 2026. The Council votes 4–1 to keep Freebee for another year and adds a $2 fare.
6. July 20. At its July 9 meeting the Council told staff to start the fare on this date. Riders get a full-screen pop-up in the app, plus push notifications and emails.

The service has also grown past the Village line. KeysNews reported that it reaches Mariners Hospital, the Good Health Clinic and the Tavernier Towne shopping center. Keys Weekly described the riders as working locals going to their jobs, seniors going to doctor appointments and visitors riding from hotels to local businesses.

How the Fare Got Approved This Summer

The Village's contract with Freebee was set to expire in June. In March the Village asked on-demand rideshare companies to bid, and two did: Freebee and Circuit. Both presented their plans and took questions from residents. A Village evaluation committee recommended staying with Freebee at a cost of $530,000.

The Council voted on June 11 at the Founders Park Community Center. Mayor Don Horton voted yes, pointing to Freebee's seven years in the Village and riders' high satisfaction. Councilman Steve Friedman said the service is needed. He also worried that charging $2 after years of free rides could drive some riders away. In the same discussion, as Keys Weekly reported, he said the vehicles aren't "nearly enough in terms of what is going on trafficwise" in the Village.

Vice Mayor Sharon Mahoney cast the only no vote. She raised concerns about Freebee's wait times and asked how the $2 figure was chosen. Then she made the point that matters most for next summer. According to Keys Weekly's account of the meeting, she said the state grant was meant to give the Village time to work out how to support the service itself.

"And we haven't done that."

The fare wasn't a new idea. The Council had talked earlier about a modest charge, around $2.50 a ride, either to lower the yearly cost or to make the state grant money last longer. What changed this year was the deadline.

The State Grant Was Always Going to End

The state grant program was never meant to pay for Freebee forever. The money behind the current year was the third and final round of the FDOT program, and it pays for service through June 2027. There was once a different plan. The Village expected Monroe County to take over the service as part of a Keys-wide transit system, but the county dropped that idea to save money after a state review of local government spending.

Here is how the money breaks down:

The arithmetic is simple. A $70,000 saving is about 13% of the $530,000 contract. Measured against the Village's own half, about $265,000, the fare covers roughly a quarter. When the state's half ends, that gap gets bigger.

The Village's overall budget shows what else that money competes with. At the final budget hearing on Sept. 28, the Council chose a millage rate of 2.65 instead of the proposed 2.7231. The Village still expects about $19.5 million in property tax revenue for the fiscal year that began Oct. 1, up from $18.2 million the year before, because the value of taxable property in the Village rose by $491 million. Day-to-day operations cost $23.9 million, and about $13.5 million of that goes to public safety. The adjusted plan also cut parks and recreation money for special events.

Statewide politics could tighten things further. At the June meeting, Mahoney said the Village might collect less property tax if voters approved a ballot measure in November. On Nov. 3, Florida voters passed Amendment 3. NBC 6 reported that it expands the non-school property tax exemption in 2027 and 2028. The Village will be deciding what to do about Freebee in that same 2027 window.

What the Mayor Has Floated

Horton has described a different kind of service. Instead of cars that come to your door, he'd like a loop where trolleys or other vehicles run along the Old Highway and pick up and drop off riders at set stops. He presented it as something he hopes the Village can do eventually.

The idea has history. Freebee started as a downtown loop of carts on Upper Matecumbe, and residents liked it enough that it grew into door-to-door service across the bridges. The current schedule runs from 7 a.m. to midnight daily, 357 hours a week. That is up from 210 hours, an expansion the Village made to qualify for the state grant.

How Freebee Works This Winter

For now, the service works the same way it did before July 20, except for the fare:

• Hours. Every day, 7 a.m. to midnight, according to Freebee's Islamorada service page. Requests have to come in at least 15 minutes before closing.
• Pickup and drop-off. Anywhere inside the mapped service boundary.
• How to request. Through the Freebee app, where the fare notice first appeared.
• Vehicles. Two Tesla Model Ys and an electric van that can carry a passenger in a wheelchair.
• Beyond the Village line. KeysNews reported that service reaches Mariners Hospital, the Good Health Clinic and Tavernier Towne.

Before you count on a particular stop, check the map in the app.

Whatever the Council decides about Freebee after June 2027 will come up at regular meetings at the Founders Park Community Center, where the June 11 vote took place.

How you get from Plantation Key to Lower Matecumbe without driving is part of what everyday life in a home here looks like. Kelsey Caputo-Frins pays attention to details like this when she advises Islamorada owners. If you're thinking about how your own home fits into Village life, Request a Valuation & Design Consult.