VIDEO · KITEBOARDING
Learn to Kiteboard in the Florida Keys
With Matt Sexton, owner · kiteboarding for over 20 years · July 20, 2026 · 3 min 9 sec
It's kind of like a ski resort — just with palm trees. Matt Sexton, owner of Grassy Flats Resort & Beach Club on Grassy Key, has been kiteboarding for over 20 years and chased wind all over the world before settling on the Florida Keys. In this video he walks the almost five miles of waist-deep flats behind the resort, explains the three-part course that takes you from your first board ride at Keys Cable Park to covering ground on the open flat, and covers when the wind season actually runs — and what you'll ride on the days it doesn't blow.
What's in this video
0:00 Welcome to Grassy Flats — a kiteboarding resort, "like a ski resort with palm trees"
0:17 Why the Keys, after 20 years of chasing wind around the world
0:33 Five miles of waist-deep flats — fall, stand up, go again
0:41 Keys Cable Park & the kiteboarding-specific Cable for Kiteboarding course
0:58 The three-part learn-to-kite course: board, kite, then jet-ski-supported riding
1:24 When the wind shows up — cold-front season, Thanksgiving through winter
1:44 Gulf on one side, ocean on the other: riding every wind direction
2:07 The sport-fishing capital of the world
2:19 More than kiteboarding: eFoils, outrigger canoes, paddleboards, kayaks
2:29 Whatever the conditions, there's a right call for the day
2:53 Come get on the water — the team handles the decisions
Transcript
Welcome to Grassy Flats Matt Sexton: Hey guys, I'm Matt Sexton, and welcome to Grassy Flats. This is a kiteboarding resort — kind of like a ski resort with palm trees. We built this place to have a very intentional setup that's going to be one of the best possible ways to learn how to kiteboard, or, if you already know how to kiteboard, to come here and enjoy a good vacation. Why the Keys, after 20 years of chasing wind I've been kiteboarding for over 20 years, and I've traveled all over the world — went to some of the coolest destinations — and I just kept finding myself coming back to the Florida Keys. And when we found Grassy Flats, it was one of the most perfect places that you could possibly get out and ride. Five miles of waist-deep flats This whole flat right behind me is actually almost five miles long, and it's waist-deep water. You can fall, stand up, get up, go. Keys Cable Park & Cable for Kiteboarding In 2011 we started Keys Cable Park, which is the only two-tower cable park in the world that has a very specific kiteboarding course. We do this course called Cable for Kiteboarding, and it's definitely the easiest possible way that you can learn how to ride a board in a very specific fashion for kiteboarding. The three-part learn-to-kite course So we've broken our learning down into a three-part course. Cable for Kiteboarding is going to teach you how to ride the board. We're going to do an Intro to Kite Flying in waist-deep water right here on the flat — that's going to teach you how to fly the kite. And then we're going to hop on a jet ski, start towing you up and down the flat, and allow you to really start covering some ground. That three-part course can get anybody into this in the most safe, effective, and efficient way possible. I really, truly believe this is the best way you could learn how to kiteboard. When the wind shows up — cold-front season Our season is really going to be based on that hurricane season and the frontal pattern that comes across the United States. So if you get to around Thanksgiving time, hurricanes are a thing of the summer past and fronts are starting to come through. The northern states are getting cold — that means we're getting ready to shred. That wind season is going to carry pretty much all the way through the winter. Gulf on one side, ocean on the other And we're in the Florida Keys — we've got the Gulf on this side, the ocean right here. So we can hit any wind direction. Ideally we can pump up and ride on these east winds to southwest winds right here in front of the hotel, but we do have boats to be able to access all wind directions. So no matter what, we can get you out there. Sport-fishing capital of the world The beauty of Grassy Key, and right here at Grassy Flats, is that no matter what — wind or no wind — we can get you out with a good activity. The last few days we've been out mahi fishing here in the summertime. This is largely considered the sport-fishing capital of the world, and we've got some of the best guides around that can get you offshore, backcountry, whatever you're looking to do. More than kiteboarding Aside from that, we're not a one-trick pony around here. We've got eFoils, we've got outrigger canoes, we've got paddleboards, kayaks, and Keys Cable Park with the Rum Runner Aqua Park just a mile down the road. Whatever the conditions So no matter what the conditions are — it's blowing 10, it's blowing 20, it's blowing nothing, it's slicked out — we're going to recommend the best possible thing to get you on the water, to have a good time, and to keep some fun going while you're on vacation. Come get on the water This isn't something you're going to have to do on your own. Our team is here to help throughout the entire process, from start to finish. So once you get an idea of what you want to do — or even if you have no clue what you want to do — just reach out to us and let us take care of the decisions based on the conditions. All you have to do is pick up the phone, call the front desk, or hit up the guys at the Florida Keys Waterman's Company here, and we'll get you booked. Kiteboarding, fishing, paddleboards, anything. We want to get you on the water.
Quick answers
Why are the Florida Keys a good place to learn to kiteboard?
How does the three-part learn-to-kite course work?
Cable for Kiteboarding at Keys Cable Park teaches you to ride the board, Intro to Kite Flying in waist-deep water on the flat teaches you to fly the kite, then a jet ski tows you up and down the flat so you start covering ground.
What makes Keys Cable Park different?
Started in 2011, it's the only two-tower cable park in the world with a kiteboarding-specific course — the easiest way to learn board skills before you ever touch a kite.
When is the wind season at Grassy Flats?
From around Thanksgiving through winter, when cold fronts start crossing the United States. With the Gulf on one side and the ocean on the other, the resort can ride nearly any wind direction — east through southwest winds work right in front of the hotel, and boats cover the rest.
What is there to do when the wind doesn't blow?
Plenty — the Middle Keys are considered the sport-fishing capital of the world, and Grassy Flats also runs eFoils, outrigger canoes, paddleboards, and kayaks, with the Rum Runner Aqua Park a mile down the road.
