Caribbean Watersports boats on the calm turquoise water of Florida Bay in Key Largo

For the Ride… Worth the Drive

A Key Largo family's love affair with the water

For more than four decades we've shared Florida Bay with travelers from around the world — built on the legacy of a true pioneer of the water.

Caribbean Watersports & Enviro-Tours has called Key Largo home since 1983. We're a family-owned operation on the calm, shallow flats of Florida Bay, and to this day every snorkel trip, sunset champagne cruise, and private eco tour is run the way it always has been: small, personal, and with a deep respect for the water and the people we share it with.

But our story starts a little earlier — and on a much bigger wave.

In dedication to our founder

Darrell McCullough

Founder & Inventor — the father of modern commercial parasailing

Long before parasailing became a postcard staple of beaches and bays the world over, it was a dangerous affair. Darrell McCullough changed that. A relentless innovator, he didn't just popularize the sport — he reinvented how it could be done safely, and built the foundation that the entire modern industry still stands on today.

The invention that changed a sport

In the early days, parasailers launched and landed on the beach — at the mercy of the wind, the crowd, and a long run across the sand. It looked thrilling. It was also risky. Darrell set out to take the danger out of flight.

“The breakthrough wasn't the parachute — it was the boat. Once the line could be let out and reeled back in from the deck, the beach take-off disappeared, and so did the risk that came with it.” — On the Winchboat system, 1974

His Winchboat introduced a powered winch mounted on the boat itself. The towline could be precisely let out and reeled back in from the boat deck, lifting passengers gently off the platform and setting them back down dry — no hazardous beach take-offs or landings, no scramble across the sand. Awarded U.S. Patent No. 3,987,746, it became the same fundamental principle behind virtually every commercial parasail operation flying today.

His commitment never stopped at the thrill. In 1998 he founded the Parasail Safety Council, publishing the sport's first commercial safety guidelines and helping turn a once-dangerous pastime into something families could trust. That safety-first instinct is the inheritance every Caribbean Watersports crew still carries onto the water.

A vintage photo of an original red Caribbean Watersports Enviro-Tours boat on Florida Bay at dusk, with two children aboard
One of the original "Caribbean Watersports — Enviro-Tours" boats on Florida Bay. The family has been sharing these waters, and raising the next generation on them, for decades.
The Carolina Moon sailing catamaran under full sail with the blue Caribbean Watersports logo on its mainsail over the turquoise water of Florida Bay in Key Largo
The same water today — the Carolina Moon under full sail on Florida Bay, carrying the next generation of guests across the bay we've called home for fifty years.

Moments that made us

  1. 1971

    Lifting off from the water

    Darrell McCullough introduces offshore parasailing platforms — moving the sport off the beach and out onto the water for the first time.

  2. 1974

    The Winchboat is perfected

    The breakthrough: a deck-mounted winch lets the towline pay out and reel back in from the boat, eliminating dangerous beach take-offs and landings. Modern commercial parasailing is born.

  3. 1976

    Patented, and shared with the world

    The Winchboat earns U.S. Patent No. 3,987,746. The deck-launch principle it established still underpins virtually every commercial parasail operation flying today.

  4. 1983

    Caribbean Watersports opens in Key Largo

    The family plants roots on Florida Bay at Mile Marker 104, right beside the historic Caribbean Club — building a business around private, personal trips on the calm shallow water of the Upper Keys.

  5. 1989

    A new home at Mile Marker 97

    The operation moves to the Sheraton Key Largo on Florida Bay — a beachfront base it would call home for more than three decades.

  6. 1996

    Down to Islamorada

    For five seasons the family runs all the watersports — including a PADI 5-Star Dive Center — at the legendary Cheeca Lodge in Islamorada, sharing the reefs of the Upper Keys with a new wave of divers.

  7. 2016

    A home at Playa Largo

    Caribbean Watersports opens at the brand-new Playa Largo Resort & Spa, an Autograph Collection by Marriott — a home base on Florida Bay for the next decade.

  8. 2017

    Weathering Hurricane Irma

    When Irma roared through the Keys, the family rebuilt, regrouped at Playa Largo, and kept the boats running — because showing people the bay is what we do.

  9. 2023

    Forty years on the water

    Four decades since that first season at MM104 — still family-owned, still private, still in love with Florida Bay.

  10. 2026

    Untethered — we come to you

    In January, Caribbean Watersports leaves its resort base and goes all-in on what it always did best: fully private trips with bayside pickups between Mile Marker 92 and MM103. No marina lines, no crowds — just your group, your crew, and the water.

  11. Today

    Among the best in the Keys

    A TripAdvisor Travelers' Choice winner and a Top 10% operator ten years running, we run private snorkeling excursions, sunset champagne cruises, and eco-tours aboard our own boats — meeting you right on Florida Bay, and carrying forward a legacy of doing it right and doing it safely.

Four decades of snapshots

From the family album

Film photos, scans and clippings from the early years — parasailing firsts, rainbow Hobie fleets, and the little red boats that started it all.

A red and white parasail lifting off behind a small boat in an early film photograph
The early days of offshore parasailing — the sport our founder helped invent.
Aerial view of a rainbow parasail flying behind a yellow towboat over green water
Up, up and away over the bay.
Crew members guiding a colorful parasail back onto the deck of the chase boat
Bringing another flight home.
Aerial photo of the resort watersports beach with a parasail boat, sailboats and swimmers
Our beachfront home at MM97 — three decades of watersports off this sand.
A 1995 magazine advertisement reading Sleep with us, Sail with us for the Sheraton Key Largo and Caribbean Watersports
1995, in print: “Sleep with us… Sail with us.”
A young man in a pink shirt at the helm of a boat with Hobie catamarans sailing behind him
At the helm, sometime in the ’90s.
The Enviro-Tours crew in white shirts standing aboard the original red inflatable boat
The Enviro-Tours crew, ready to run the backcountry.
A guide pointing out wildlife to a family aboard the red Enviro-Tours boat on calm water
The original Enviro-Tour — private, personal, unhurried.
Hobie catamarans with colorful sails gliding through a mangrove creek in an old film photo
Threading the mangrove creeks under sail.
Aerial view of a fleet of Hobie catamarans sailing over the shallow flats of Florida Bay
The fleet from above, out on the flats.
Hobie catamarans silhouetted against a blazing orange and purple Key Largo sunset
Hobie sunset, straight off a postcard.
A mother holding a baby with two young girls aboard a sailboat in a vintage family photo
A family raised on the water.
A Taste of Paradise magazine feature showing waverunners and sailboats in the Florida Keys
“A Taste of Paradise” — the fleet makes the magazines.
A 2002 Hobie Getaway advertisement calling the catamaran a 16-foot family vacation
2002: Sailing World crowns the Hobie Getaway — “a 16-foot family vacation.”
A seaplane floating on shallow turquoise water beside the red Enviro-Tours boat in the backcountry
Backcountry traffic — a seaplane drops in.
A guide standing in the red Enviro-Tours boat beside a small mangrove island on glassy water
Pulling up to your own island.
A guide and two children peering over the side of the red Enviro-Tours boat into the mangroves
Little explorers in the mangrove nursery.
The original Enviro-Tours brochure spread with photos of dolphins, an osprey and guests aboard the red boat
The original Enviro-Tours brochure.
Looking down the towline from a parasail at the boat far below on turquoise water
The view from the chute, halfway up.
A parent windsurfing with a small child sitting on the front of the board
Learning the wind early.
Four kids standing arm in arm on the shore watching Hobie catamarans sail past
The next generation, sizing up the fleet.
An artist painting at an easel on the beach as Hobie catamarans come ashore behind her
Pretty enough to paint.
A sailor leaning out from a Hobie catamaran with a full rainbow-striped sail
Full rainbow, full send.
Guests laughing aboard a Hobie Wave catamaran with yellow and red sails on turquoise water
Aboard the Wave, mid-laugh.
A magazine page reading Florida Sunshine and Hobie Heat Make Waves of Winter Warmth in Key Largo
“Florida sunshine and Hobie heat” — another magazine moment.
The cover of HOTSHOTS photography magazine featuring a rainbow-sailed Hobie catamaran
Cover boats — the fleet lands the HOTSHOTS cover.
A white sailing catamaran resting on her mooring under a blue sky
On the mooring, ready for the day.
A lone sailboat on glassy water under a pink and lavender sunset sky
Evening glass on Florida Bay.

What hasn't changed

The way we've always done it

Safety first, always

It's in our DNA. The whole family business was born from making time on the water safer — and that mindset guides every trip.

Family-owned

No franchise, no call center. When you book, you're dealing with the same family that's run this since 1983.

We come to you

Private bayside pickups between MM92 and MM103 — no crowded marina. No dock of your own? Our port of call is Bayside Grille at MM99 bayside.

Respect for the bay

Florida Bay is our backyard. We tour it gently, the way you'd treat something you want your grandkids to see.

Come be part of the next chapter

Four decades in, we still get a kick out of showing people the best of Key Largo. Book a private trip and see why it's worth the drive.

Book Online →

Or call (305) 852-4707

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