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? 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