Learn to Teach Wakeboarding, Kiteboarding, Efoiling, Sailing, and Wrangle people on our Aqua Park!

Watersports Coach (“Goon”) — The Lagoon on Grassy Key & Grassy Flats Resort! | Florida Keys

The Deal

Ever wanted to spend your days teaching people to wakeboard, kiteboard, foil, and sail — in the middle of the Florida Keys — and get paid to level up your own skills while you do it? Welcome to life as a “Goon” at the LaGoon on Grassy Key!   Goons in training start as an Aqua Guide on our inflatable Rhum Runner Aqua Park, dispatching riders and selling the good life to guests fresh off the highway. From there, the sky or sea is the limit: master operating our system 2.0 Cable systems and you’ll level up to a Cable Operator / wakeboarding coach and with learn the basics and pass our training programs in kiteboarding, wingfoiling, sailing, and paddlesports, to become Wind and Boardsports / waterman Instructor — each level comes with higher hourly pay and serious commission potential. If you’re an outgoing waterman or waterwoman who wants to learn from the best and get paid to do it, keep reading.

What You’ll Do

No background?  No problem.. have experience? We’ll put you in the right program!

• Start as an Aqua Guide on the Rhum Runner Aqua Park — the largest inflatable waterpark in the Florida Keys — running dispatch, guiding guests, and selling our watersports programs

• Train up through our in-house coaching pipeline to teach wakeboarding, kiteboarding, wingfoiling, efoiling, outrigger canoe, sailing, and more at our full-service Waterman’s School 

• Progress to Cable Operator and Wind and Boardsports Instructor, unlocking higher hourly wages plus commission-based pay

• Work as a “Swiss Army knife” across the property — tasks vary day to day, and hospitality-side shifts are available if you want extra hours

• Help guests fall in love with the water and the tropics, one lesson at a time

Who We’re Looking For

Outgoing, adventure-minded people who want to actually learn watersports at a high level — not just work near the water. Whether you’re a total beginner hungry to learn or already riding and want to sharpen your teaching chops, if you’ve got the hustle and the personality to match, we want to talk to you.

Where

The Lagoon on Grassy Key, in the town of Marathon, Florida Keys — home to Keys Cable Wakeboard Park since 2011 and now the largest waterpark in the Keys. Our sister property, Grassy Flats Resort and Beach Club, runs like a ski resort — with palm trees. Together, under owner/operator Matt Sexton, we’re the last family-owned action sports and hospitality operation left in the Florida Keys: a 38-room oceanfront hotel, 3 restaurants, a cable wake park, a massive inflatable aqua park, and a premier Waterman’s School offering kiteboarding, wingfoiling, efoiling, outrigger canoe, fishing charters, and sailing.

When

Year-round position, Seasonal Available as well!. Start dates flexible — reach out and let’s talk timing.

Once you’re here

• On island staff housing available for experienced candidates

• Company food & beverage programs at all outlets

• Watersports equipment usage programs

• Employee deals — including blowout pricing — on new, used, and demo gear

Why Grassy Key

Because nowhere else lets you learn this many watersports at this high a level, on one property, while getting paid to do it. This isn’t a summer job by the water — it’s a real coaching path with real earning potential (commission stacks on top of hourly as you level up), backed by a small, family-run team that actually wants to see you grow. Come for the riding, the saltwater, the community, and the chance to become one of the best all-around watersports coaches in the business.

Ready to become a Goon? Apply now and join the crew at The Lagoon on Grassy Key.