PLAY · KITEBOARDING LESSONS
Kiteboarding Lessons in the Florida Keys
A three-step progression system, built backwards from what actually works, on one of the best learning flats on the planet.
There is a version of this sport that most people never find.
They take a lesson somewhere warm, get dragged around by a kite for a weekend, and walk away thinking kiteboarding is harder than it looks and probably not for them. That's not what you'll find here.
Matt Sexton built Grassy Flats because he knew what the right version looked like. He had ridden every destination worth riding, competed, and coached enough people to understand where the learning breaks down. When he bought a stretch of Grassy Key and started building a school, he built it backwards from that knowledge. The method came first. The flat water and the consistent wind were already there. The rooms, the food, the sauna, the cable park, those came because new and experienced kiteboarders need somewhere to relax and connect with the community when they are not on the water.
This is the only kiteboarding resort of its kind in the continental United States. There is simply nowhere else where the instruction, the conditions, the infrastructure, and the culture have been built together from the beginning by someone who actually rides.
The flat sitting out front is one of the most underrated progression environments on the planet. I've also traveled to every kitesurfing hot spot. I choose to ride and film tutorials here because there is nowhere else in the continental USA where you can kick it on a sandbar in boardshorts with turquoise water and easy-to-learn wind. Matt and I have both been to the spots everyone knows. The Keys keep showing up as our favorite answer when the question is where you actually want to spend a week getting better.
— Ryan (Rygo) Goloversic
THE METHOD
The Three-Step Progression System
Most people who quit kiteboarding quit in the first few hours. They are in deep open water, getting dragged downwind, fighting a kite they cannot control yet, standing on a board they have never ridden. Too much at once, and they never get the good part.
So we built it in three steps — learn one thing, then the next, then put them together.
You start on the cable at the wake park, no kite, just you and the board, learning to ride. The board is the hardest part of this sport, and almost nobody tells you that. Most of our team has been teaching for 20-plus years, and the students who put in cable time progress so much faster, with none of the pain — it's a total cheat code. Then we add the kite, in the shallows and in the air, until flying it feels like nothing. By the time we put you in open water with both, you already know what your feet are doing and what your hands are doing, and it clicks.
The shallow water out front is the other cheat code. No fear of blowing out to sea, no deep water panic — if something feels off you just stand up and relax. You progress when you're calm, not when you're scared. It doesn't hurt that you'll have an instructor on a jetski walking you through everything step by step. And the part nobody else can offer: Matt owns this place and he's still out on the water teaching alongside Davo most days.
STEP 1
Cable for Kiteboarding
$249 · 1–2 people
A 30-minute classroom session on how the sport works and how the kite generates power, then about an hour on the cable wake park building board skills — edge control, upwind riding, board starts, transitions — with no wind variable and no kite overhead. The cable handles the pull. You handle the board.
STEP 2
Intro to Kite Flying
$249 / 1 · $299 / 2
Two hours with the kite — on the ground, in the air, and in your hands. Setup and breakdown, reading the wind window, controlling and releasing power, self-rescue, body dragging, one-handed flying. No board. Just the feel and the reflex before you add riding.
STEP 3
Kiteboarding Lessons
$150/hr · 1 · $200/hr · 2
Where it comes together. Three-hour goal-oriented sessions, one instructor to one student, booked daily on conditions. Additional riders $100 each. Beginners arrive with board skills and kite feel already in their body; intermediate and advanced riders book directly here.
GRADUATION
Guided Downwinder — Coco Plum or Curry Hammock
$200 without instruction · $300 with · per 5-person trip
This is what you are working toward. A stress-free downwind run to Coco Plum or Curry Hammock with a shuttle waiting at the other end — cold drinks and a ride back to Grassy Flats. No logistics, no car-shuttle arrangements, no worrying about what happens if something goes wrong. Most people remember it longer than any other session of the trip. The Middle Keys flat is extraordinary when you are riding it with enough skill to actually experience it rather than survive it. That is the difference the progression system makes.
CONDITIONS
What the conditions are actually like
Fifteen to twenty knots of clean wind out of the north and east, warm air, warm water, boardshorts year round. That is the sweet spot the Middle Keys sits in from November through April, with December and February through April being the peak of the peak.
The flat here is wide, protected, and runs three shades of blue depending on the depth and the time of day. Shallow enough to walk out when something goes wrong. Deep enough to crash safely when you are pushing limits. The channels that open up in every direction are one of the reasons experienced foilers keep coming back.
This is not a sandblasting thirty-knot destination. It is not a lottery of light and variable days. It is consistent, warm, clean wind over flat water with the sun on your back. For learning and for progression it is close to ideal.
When the wind is down
Light wind days are not lost days here. The cable park at the Lagoon runs regardless of conditions. An eFoil session builds the foil feel that carries directly into kite and wing progression. The fishing grounds offshore open up. The backcountry calls. Talk to the team and they will shape the day. If conditions are not suitable on your booked lesson day, we will work with you to reschedule or pivot. Nobody wants you sitting on the beach watching a flat ocean.
WHO IT'S FOR
Who this is for
Beginners, no board experience
The three-step system was designed for you specifically. You don't need to have stood on a board before you arrive — the cable park handles that. Most people who go through the full progression here are riding independently by the end of a week.
Intermediate riders
Been riding a season or two and feel stuck? Flat water with consistent wind and real coaching will move you faster than another week at your home spot. Tell the instructor exactly where you keep getting caught.
Advanced & freestylers
Matt was a professional kiteboarder. For serious coaching on jumps, transitions, and freestyle technique, book advanced sessions and have the conversation when you arrive. The instruction goes as deep as you need it to.
MAKE IT A TRIP
While you're here
The lessons are the reason you came. But the rest of the property exists to make the trip better.
→ No-wind days → eFoil rentals & lessons — foil feel that transfers directly into kite progression
→ Post-session → sauna on property. After two hours on the water this is not optional
→ Traveling with family → the Aqua Park & cable park at the Lagoon handle everyone from six-year- olds to serious wake riders
→ Catch something on a charter → the Rhum House kitchen handles the cook-your-catch. A dinner you'll remember
→ Stay & ride all week → ocean-view rooms. Stay on property and the whole thing gets easier
→ Curious about wing foiling → its own progression path and page. Different sport, same flat
A DAY HERE
What a real day in the Florida Keys looks like
The best days in the Florida Keys are not planned. They are read.
Wind or calm. Offshore or in. Moving or still. The Keys have always rewarded people who know how to follow that lead. There is a pace down here that takes about half a day to find and the rest of the trip to enjoy. Once you find it you will understand why people who come here once tend to spend the next several years trying to get back.
The morning starts early if you want it to. The light on the water at six or seven in the morning is something that belongs specifically to this place, low and golden and hitting the flats in a way that makes everything feel unhurried and enormous at the same time. Paddleboard out before the wind picks up. Take a kayak into the backcountry. Grab coffee and something real to eat and watch the day make up its mind.
By mid-morning the conditions have usually declared themselves. Wind up means the kiters are on the water and the energy shifts across the whole stretch of the Middle Keys. Calm means the charter boats are heading out and the offshore grounds are open. Either way the day has a direction and the Keys have a way of making whatever that direction is feel like exactly the right one.
The middle hours are where the Keys show you something most destinations never figure out. There is no rush to the afternoon. No checkout pressure, no scripted activity rotation. The tiki bar, the pool, the water right there in front of you. A long lunch that becomes an early apres. Live music starting at five on a rooftop with a cold drink and the sun dropping over the Gulf. This is not filler. This is the whole point.
Dinner in the Keys at its best means eating something that was in the ocean that morning. The hook and cook tradition here is real. Catch it on a charter, bring it back, eat it that night. Or sit down to a proper meal with a cocktail program worth lingering over. Either way the evening is unhurried and the conversation is good because people who have spent themselves on the water all day tend to show up to the table as their best selves.
In bed by nine. Up early tomorrow. That is a Keys day. And if you do it right, one of them is never enough.
ON PROPERTY
What can you do at Grassy Flats?
The short answer is more than you will get to in one trip.
Kiteboarding and wing foiling are the heartbeat of the watersports operation. Matt was a professional kiteboarder. The instruction here is serious. Beginners learn on the cable before they ever touch open water. Advanced riders work with coaches who have ridden everywhere and know exactly what this flat can teach you.
Wakeboarding and the Aqua Park live at the cable park behind the mangroves. Protected, consistent, and running regardless of conditions. The Rhum Runner Aqua Park is the inflatable ninja warrior course on the water that sells out every hour on the hour during peak season. Put the kids on the five o'clock session and thank us later.
Paddleboards and kayaks are included with your resort fee. Take them north to the sandbar, south into the backcountry, or nowhere in particular. The sandbar sail runs on the Hobie Cat with one of our captains and is one of those experiences that works for every age and every kind of traveler.
Fishing charters run private. Not fifty people on a party boat. You, your crew, a captain who knows these grounds, and whatever the ocean decides to give you that day. Bring it back and eat it that night.
Outrigger canoe, raceboard paddling, wing foiling, sailing lessons. The list keeps going. Every activity has its own page with deeper information on what to expect, who it is for, and how to book.
FAQ