RESOURCES · BACKCOUNTRY KITEBOARDING
Can you charter a boat to go kiteboarding in the Florida Keys?
Yes. You get on a boat in the morning, run out into water with no road to it, and ride a flat with nobody else on it. Matt Sexton owns Grassy Flats, he bought a boat specifically to do this, and he has ridden most of the places on earth that people fly to for wind.
Here's what it actually looks like when you're standing on the deck.
4 HOURS
Morning or afternoon session
6 PEOPLE
Passenger capacity on the boat
SUGARLOAF
Meet at Sugarloaf Marina
WIND-LED
The route depends on the day’s wind
Water so clear and so shallow the boat looks like it's floating on nothing. Sand going out in every direction, a mangrove key sitting low a half mile off, and the wind coming across it clean with nothing to break it up. No condos. No jet skis. No lineup, because there's nobody else out here. The flat next to the boat is ankle deep, warm as a bath, and you can stand on it while your buddy hands you a kite. Six inches of water and blue in every direction, and the only sound is your lines and the boat rocking a little.
Then you go. Nobody in front of you and nowhere you have to be.
Matt puts the whole thing in one frame:
And he means the comparison seriously:
The rest of this page is the mechanics. How the day runs, where the boat goes, what you can build into it, who's out there with you, what it costs, and who should not book this.
THE DAY
How does the charter day actually work?
You drive down island in the morning and meet the boat at Sugarloaf Marina. That drive is part of it, early light on the water on both sides of the road, coffee, nobody talking much.
Sessions run four hours. Morning trip or afternoon trip, and the boat takes six passengers.
If you want food and drinks out there, you say so the day before:
Then it's out into the backcountry, and where you end up depends on the wind that day.
THE FLATS
WHERE DO YOU RIDE?
Backcountry
Backcountry means the maze of flats, channels, sandbars, and mangrove keys behind the island chain, on the Gulf side. Shallow, protected, and the only other people out there are flats guides and lobster boats.
The flats
The flats are what you ride. Hard white sand and turtle grass running out for a mile, ankle deep in places and waist deep in others, and the wind comes across it with nothing in the way. No chop worth mentioning. You can stand up anywhere.
The sandbars
The sandbars are what you ride to. At low water they come up out of nothing and turn into a beach in the middle of the ocean, no trees, no buildings, nobody. That's where the boat parks and where the day turns into a day instead of a session.
Matt names two spots without hesitating. Marvin, and the Contents.
That downwinder is what good riders ask for once they understand it's on the table. The boat leapfrogs you, the water changes color underneath you the whole way, and you finish somewhere completely different from where you started.
Between the two you get rays kicking up sand ahead of your board, tarpon rolling in the channels, frigatebirds up high, and sharks you will see and not care about by the second hour.
THE EXPERIENCE
What can you build into a kiteboarding boat trip?
There is no fixed product here. Matt's whole model is that you tell him what you want and he builds the day around it, and the frame he uses for it is heli skiing. You're paying for access, and once you have the access, the day is yours.
So here's what people actually ask for. Pick one, combine two, or describe something that isn't on this list.
The sandbar day
Ride the flat in the morning while the wind is good, then park the boat on a bar at low water and get off. Waist deep, warm, cooler open, everybody standing around in the middle of the ocean with no land in sight. Ride again in the afternoon if you still want to. Half the people who do this remember the sandbar more than the session.
The crew charter
Six seats. Two of you ride, four of you don't, and nobody has a bad day. The riders get a flat to themselves and the rest get a sandbar, a cooler, snorkel gear, and water clear enough to see your own feet in four feet of it. This is how a full day gets booked, and it's the version almost nobody realizes they can ask for.
The downwinder
Contents to Marvin, boat trailing you the whole way. Miles of water, no repeats, and you finish on a sandbar with the boat already there.
Double session
Morning trip, food, afternoon trip. Two sessions in different water because the wind moved and Matt moved with it.
Chase the wind
No spot picked in advance. You run all day and ride wherever it's actually good, which some days means three different flats.
Kite and fish
Rods on the boat. Ride in the morning, fish the channels on the way back, and take what you catch to the market and the Rhum House that night. Two programs, one day.
Bring a camera
Matt has been getting kite film made out here since the early Slingshot days. If you want real footage of yourself riding water nobody has seen, say so before you go and it gets planned for instead of shot by accident.
Food and drinks
Food and drinks from the market, ordered the day before and loaded on the boat before you show up.
The eFoil version
Same boat, same water, different sport, its own page.
Matt's answer to almost every version of "can you do this" is the same:
The thing to understand is that none of the above is a package with a name and a price. It's a boat, a captain, a guide, and a day. What you do with it is the conversation.
THE CREW
Who's on the boat with you?
A captain and a guide, and Matt draws a hard line under that difference:
You're a long way from a ramp out there. Gear gets caribou ried as backup, somebody on that boat rides at a level well past yours, and if your kite goes down in a channel with current running, that's a problem that has already been solved a hundred times by the people standing next to you.
ON THE WATER
What is it actually like out there?
Ask Matt for a story and you get this one.
He rolls up on a flat and there's a bald eagle sitting on the sand by itself, alone in the middle of a postcard. Then the water starts moving.
Six guests standing on the boat, wide eyed, watching a shark beach itself to eat. And then somebody asks the obvious question, which is where exactly are we riding.
That's the trip. National Geographic happening forty feet off the bow, and then you go ride ankle deep water next to it.
The other thing that happens is the part after. You come back in and everybody who stayed at the resort wants to know where you were.
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COST
What does a kiteboarding charter cost in the Florida Keys?
Half day is $600 to $800, and the reason it's priced there is the boat. It runs down island to Sugarloaf, gets launched, and burns fuel getting you somewhere with no road.
A full day built around a specific ride, a downwinder or a multi spot day, is $1,200 to $1,300.
Back to back morning and afternoon sessions are priced separately, not as one day.
READINESS
What do you need to be able to do to book this?
THE FIT
Who should skip this?
If you're learning, skip it. Learn on the flat in front of the resort where you can stand up, walk in, and try again in ten minutes. Book the boat next trip when the payoff is worth it.
If wind is the only thing you care about and you want the most sessions per dollar, you don't need a boat. Ride out front, ride every day, and put the money into staying longer.
And if you want the cheapest version of a boat trip, Matt already told you those guys exist. This isn't that.
SEASON
When is the season for this?
November through April, with December and February through April as the peak. Fifteen to twenty knots, warm water, boardshorts. Full breakdown lives on the watersports pillar, so this is the short version.
The other thing worth saying plainly, and Matt says it better:
FAQ