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Cayman Island Kiteboarding Guide

Jan 6, 2010

Author: words by Damien LeRoy, photos by Steve Broadbelt

“When you jumped you wanted to stay up there to check out everything beneath the sea, huge coral heads, beautiful seagrass beds and tons of stingrays!”—Damien LeRoy

The Cayman Islands is one of the Caribbean’s greatest treasures. What sets the Cayman Islands apart from the rest of the Caribbean is its unique location just below Cuba. This provides an exclusive look to the Caymans you simply can’t find in the Caribbean chain. Its diverse set of world-class activities including kiteboarding, surfing, skateboarding, scuba diving, snorkeling, and, yes, an active nightlife! Three small islands: Grand Cayman, Cayman Brac and Little Cayman lie on the turquoise waters of the western Caribbean, only 480 miles south of Miami, offering boarders and watermen a dream location.

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    We have traveled around the globe trying to find the most amazing kiteboarding vacation, but what does the “best trip ever” really include? We have found epic kiteboarding spots before, but not much else going on. We have found epic surf, but little wind. We have gone on great scuba adventures, but nowhere to launch kites! Grand Cayman offered us everything, that is why we can say it was truly the “best trip ever.”
    Damien LeRoy, Jon Modica, Melissa Gil and Fritz Otiker flew to Grand Cayman, without knowing this would be a full-on, action-packed and epic long weekend. What could be more fun than traveling with friends to a beautiful tropical island in the Caribbean to kitesurf on turquoise, translucent flatwater, ride epic waves over the reef, dive with sharks on the edge of the reef, snorkel and kite with hundreds of stingrays, and on top of that visit a sick surf and skatepark?
    We flew into Grand Cayman Airport on Wednesday night and were welcomed by Mike and George with the Kitehouse at Grand Cayman, which is partnered with Ocean Frontiers, Grand Cayman’s best dive centre, to bring together world-class scuba diving and world-class kiteboarding. The following morning we were up at the crack of dawn and drove past the Blow Holes to East End. We met with Moe and Steve at Ocean Frontiers and drove the boat out to the shipwrecks to shoot with the sunrise. Despite being half awake, the riding was amazing and the spot was spectacular. Damien and Melissa were first out riding 10m kites, on flatwater, in a beautiful sunrise, with 80 degree water and 80 degree air. Basically it was one of the most pleasant sessions of their lives. Of course Damien thought he needed to spice things up a bit and jump over the most rusted and jagged shipwreck sticking out of the water! Once the sun was up we did a downwinder to Ocean Frontiers and Compass Point Hotel. Jon surfed the boat’s wake as we cruised downwind. Once we got to the dive centre Damien used the docks as a slider park.
    On Friday we drove to Gun Bay where the barrier reef protecting the bay and the shallows allow for perfect turquoise flatwater. The beautiful white sand beach has plenty of room for launching the kites. Later that day we cruised downwind, heading north to a spot where the reef comes closer to shore to ride waves. The downwinders were spectacular, the views of the coastline were breath-taking, and the ocean has so many colours, you can see every imaginable tone of blue, from deep blue to turquoise to almost purple! And when you jumped you wanted to stay up there to check out everything beneath the sea, huge coral heads, beautiful seagrass beds and tons of stingrays. And kiting wasn’t the only fun, the waves were great for regular surfing and when the wind was light in the afternoons we would go for a surf session at Blow Holes.
    The next day we headed out on the boat to Rum Point and Stingray City. We enjoyed the boat ride just as much as the kiting as we gazed upon the changing shoreline from beautiful white sand beaches to big, rocky 20 foot cliffs. Once we got to Rum Point we couldn’t believe how beautiful the water is there, it makes you want to jump in and swim and play all day long. Just a couple of miles from Rum Point lies a big sandbar called Stingray City, named after the hundreds of stingrays that hang around and feed in this sandbar. Back in the day fisherman would come back after a long day of fishing out in the open ocean and clean their fish at this sandbar, the food attracted the stingrays and so they became accustomed to being close to humans and feeding. As soon as we jumped off the boat you could see the stingrays coming to check you out. Talk about a close encounter with sea creatures, these stingrays have no fear and come as close as they can get, rubbing themselves on you. We thought this was the greatest underwater experience, but we had no idea what was to come with our diving adventure, it was a diving experience was like none other.
    Between the friendly and knowledgeable staff, well-equipped and comfortable dive boats, and the great dive site selection, Ocean Frontiers offers a five-star dive operation. Diving out in the open ocean of the East End is very exciting and Ocean Frontiers offers visits to sites that no one else goes to. As soon as we hit the water we realized why this place is known worldwide for its diving. The visibility was amazing and the reef wall seemed immense and majestic, standing steep and going down well below 100 feet. The coral reef was full of life and healthy. Swimming through canyons and tunnels was a rush; we saw colourful fish and coral in every direction, huge grouper, moray eels and lobster. As we turned out of one of the canyons we came to a small spot of sand on the bottom where we stood to gaze upon the most thrilling of all the sea creatures yet. Two reef sharks where roaming around. We thought we would be scared of being in the water with a shark, but the experience was really unimaginable. There was something amazing about being next to this incredible animal in its element. Somehow peace and happiness find you in this underwater world as you listen to your own breathing and praise the many wonders of our planet.
    On our final day the wind was out and the waves were small so we decided to go check out the Black Pearl Surf and Skate Park, which has the world’s largest free-standing wave and a 6,200 sp. ft. skatepark. We had so much fun. Jon was a natural; he rode that wave like he had been doing it for years and he even got barreled!
    We stayed at the Compass Point Dive Resort, which has all the comforts of home and is fully equipped. We literally stepped out of our room everyday for a full day adventure of kiting, snorkeling or diving. It was a great way to experience Grand Cayman, which is blessed with warm, steady wind nearly year-round, turquoise, crystal-clear water and a lot to do no matter the weather.

Cayman Islands Kiteboarding Guide
Closest Airport: GCM
Best Winds: October to March but wind year-round
Average Kite Size: 10 m
Cost Factor: Medium, high
Local websites: Ocean Frontiers,, Black Pearl Surf and Skate Park:
Local Schools:


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