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Liveaboard Life In The Keys Isn't The Easy Ride You Might Think. Will State Make It Harder?

A photograph of sailboats in Key West harbor
Mark Hedden
The city of Key West estimates 250 to 300 boats are "on the hook," anchored around the island. The biggest community is in Key West Harbor.

One of the last ways to live relatively cheaply in the Florida Keys is on a boat, especially "on the hook," or anchored out but it's not the idyllic easy life that you might imagine.

All day long at a dock tucked into a city-owned marina in Key West, little boats come and go. They're dinghies, small boats that carry people from their larger boats anchored offshore onto the island.

They're coming in for supplies, or to see friends. Kathy Gregory comes in to work. She’s a restaurant manager at Blue Heaven.

She got to Key West 15 years ago — she came here to buy a boat.

"And when I got here I realized I didn't know enough — and that's when I settled down in Key West," she said.

She’s lived on that boat near Wisteria Island in Key West's harbor almost the whole time. She's anchored out, or "on the hook" as it's called, and has raised her son out there.

Gregory says that life, where you have to haul out everything you need, can be tough.

"But then there's the beautiful things. The turtles that come up near your boat and the sunsets. And even the challenge of getting in and out in the rough weather — I think I like those kind of challenges," she said.

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The city estimates there are 250 to 300 boats on the hook around the island. The biggest community is where Gregory lives, around Key West Harbor.

"Freedom and social responsibility go together and I think out there you have that. Everyone's got to kind of take care of themselves and therefore everyone helps take care of each other," she said.

Gregory says part of that social responsibility is making sure boats stay safe. If they're not kept up or abandoned, they can break loose, hit other boats, or spill fuel and sewage that can damage seagrass and mangroves.

About six weeks ago, Gregory says she called the state to report a derelict vessel.

"It's abandoned, there's no one's personal stuff on it. They came a couple days later and put a red tag on it and over a month later it washed out to sea," she said.

An image of Kathy Gregory, who lives on a sailboat anchored off Key West and is the manager at Blue Heaven restaurant.
Nancy Klingener
Kathy Gregory has been living on a sailboat anchored off Key West for 15 years. She's the manager at Blue Heaven restaurant.

This year's state legislative session includes a bill that would create a program that would help prevent boats from getting to this point — from becoming what they call derelicts.

One version of the bill also requires that boats in the Keys couldn't anchor in one place for more than 90 days. So people like Gregory would have to haul up and keep moving.

The state officer in charge of boating and waterways came to a city commission meeting a few weeks ago and faced a crowd of Key West liveaboards wearing t-shirts that said "I AM NOT A DERELICT. "

Major Rob Beaton from the Florida Fish and Wildlife Conservation Commission said people who take the time to show up to a commission meeting are not who the state is worried about.

"The folks that we're concerned about are the ones that are swapping boat on a bar napkin and not registering. And then they just abandon the boat. And now the taxpayer's burdened with having to remove that boat. And the environmental cost," he said.

Monroe County spends an average of $238,415 a year removing derelict vessels. It started the state's first turn-in program, where boat owners could voluntarily surrender their vessels before they sink and turn into marine debris.

Not The Fantasy You Think It Is

The liveaboard life can sound like a fantasy like the Matthew McConaughey movie "The Beach Bum" — which actually filmed on one of the boats on the hook off Key West a couple years ago.

But it's not always so easy. Michael and Amy Moore were counting the days until a captain arrived to pick up the boat they've been living on, anchored off Key West, since the beginning of the year.

"The folks that live out there full time — I don't know how they do it," Michael Moore said.

He said his lines have been tangled up in old moorings three times. It's hot out there. The Jet Skis buzz by. And it's no fun when it's blowing hard.

And even if they'll be gone before any new laws take effect, Amy Moore said she doesn't think the 90-day anchoring rule is a good idea.

"This is your labor force here. People can't afford to live here so they have to live out there and then you're going to make it harder for them to live out there?"

Liveaboard life is one of last ways to live relatively cheaply in the Florida Keys is on a boat, especially "on the hook."

Gregory said she wouldn't live on land, even though there's always something to fix on the boat. She just spent three days fixing a cut-off switch for her propane tank.

"At the end of that three days, all that frustration turns into, like, empowerment," she said. "I definitely don't think it's for everyone but there is the beauty of the struggle."

Nancy Klingener was WLRN's Florida Keys reporter until July 2022.
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