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Shelter Island, New York Kiteboarding

Jun 18, 2007

Author: words and photos by Jason Wolcott

As we round the outer tip of the jetty in the Boston Whaler, we leave the chop of the main channel behind. The gut-jarring ride is now forgotten; it feels like we’re sliding across a blanket of silk. The boat is quickly beached, and kites are rigged with great anticipation. We are racing to be the first to slice through the glassy water with perfect nine-metre wind.

Jon Modica is first on the water, and he starts throwing powered Slims, crazy Mobe 5s and his signature S-bend to Blind. Damien LeRoy is not far behind. Jon and Damo are pushing each other to try things I’ve never witnessed before. Damien rides past and tells me to shoot a sequence on his next tack. As I hold the trigger down, he sends a giant Kite Loop Slim Chance and sticks it perfectly. I laugh out loud at how sick that last trick is, and suddenly it all comes into focus: We are in New York, and we are scoring the sickest flatwater session I’ve ever imagined.

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Long Island, New York, is a kiteboarding paradise the world has yet to stumble upon. For most, New York is a big city that exists as just another part of the northeast. But for Jon, a pro rider, Long Island is the perfect training grounds. I met Jon a few months back during a travel story to Costa Rica. My journey to Long Island began one night sitting in a little restaurant in northern Costa Rica where Jon had indulged in a few cervezas. I took what he said with a grain of salt.


“Seriously, you really need to come up to Shelter Island,” Jon kept saying. “It is the sickest spot and my favourite training grounds.”
I heard this a lot that night, dismissing it with a call to the bartender for another round. A few weeks after I returned from Costa Rica, Jon sent me images and video clips of his spot. He insisted I come out to shoot a travel story with he and Damien.

Pulling up to Jon’s parents’ summerhouse on Shelter Island, I start to realize why Jon wanted us to come out. The island is totally different from the New York I had expected. I learn quickly that sailing is life on Long Island. Everyone sails here. We unload our gear, and Jon explains that his parents are a few hours north at a sailing regatta supporting their eldest son, Charlie, who is on the U.S. sailing team. Charlie and his crew are going for gold in China in a few years. Jon gave up a sailing scholarship at the University of Connecticut to pursue his dream of being a pro kiteboarder.

I once asked Jon how he got into kiting. He told me about seeing the sport for the first time and starting a sailing club where he taught youngsters to sail in order to earn money to buy his first kites. Damo and I settle into the bunkhouse and quickly fall asleep, dreaming of what lies ahead.

Morning light awakes the bunkhouse residents. “Good breeze,” Jon says, as he digs through the fridge. We quickly find ourselves loading up the Boston Whaler and heading for the jetty. The Greenport jetty is one of the best flatwater spots I’ve ever seen. A 15-foot-high rock jetty sticks out a quarter mile into the main channel and creates the most silky-smooth butter you’ve ever seen. We quickly throw everything overboard, and Jon throws up his factory-fresh 12 m2 Switchblade 2 and makes a few tacks.

It’s light and a little gusty, but Jon has a plan. We derig, jump back in the boat and head three miles to Orient Point. The wind has filled in enough to ride, so the boys rig up and head out on a downwinder through the four-foot chop of Sunday madness, boats of all shapes and sizes dodging the pair of kiteboarders. After four miles of chop, they flag me in to pick them up on a little island. They land their kites on the front yard of a giant estate.
I ask Jon if people get upset when someone launches and lands on their property.

He smiles and says, “The people are all pretty friendly, and the worst that might happen is they ask you in for brunch.”
After lunch we head back out to Orient Point to find good 12 m2 wind and smooth flatwater. With a classic New England lighthouse as the backdrop, Damo and Jon quickly fill my four-gigabite compact flashcard with big Kite Loops, Slims, KGBs and every other wakestyle trick in the book. After shooting for three hours, we head back to the house and jump in the car to grab some pizza before passing out.

The next day we set out again in the Boston Whaler to ride at the jetty. The conditions are not right for photography, so I join the boys and ride butter-flat water for my first time. Learning to kite at C Street in Ventura, California, I had no idea how fun riding butter would be. The sound of the water coming off the rail as you slice through at speeds I never thought possible is awesome. After riding for an hour, Jon decides it’s a good day to pull out the slider.

The sun finally comes out, and it’s time to go to work. Damo and Jon throw down high-powered wakestyle stuff when I start yelling at them to one-up each other. Damo hucks the first Kung Fu handlepass I’ve ever seen and sticks it clean. Jon comes back with insane powered Mobes and Slims. It is incredible watching the two push the limits of kiteboarding. We then move on to the slider, which holds Damo’s attention for about 10 minutes.

“It’s time to jump that jetty,” he says, riding past me.

I start laughing because I know I’m about to see the maniac in Damien do something special. After a few tacks in front of the jetty to check out the wind at the takeoff point, Damo sends a huge air and floats over the huge, sketchy structure with ease. Damo is nuts. We ride until dark, friends sharing space on the water. That night, Mrs. Modica cooks us a New York–style steak and chicken dinner with all the trimmings: rice, beans, salad, cornbread, the works. Fed, bloated and tired, we crash once again in the bunkhouse.

The day begins with the lightest wind of the trip, so we get up and go into town for breakfast at Pat & Steve’s restaurant. Pat & Steve’s is an excellent place to relax and soak in the New York atmosphere. After breakfast we take the Whaler out for some wakesurfing behind the boat and have a few laughs as we all get worked over and over again.

We almost lose hope of some breeze when we notice whitecaps building in the channel. We bolt back to the house to trade the surfboards for kite gear. Two of Jon’s friends from Florida extend their stay to hang out with us. T.J. Izzo is one of those comedian types who always makes you laugh. He had flown a trainer kite once, and since the wind is light, Damo grabs him and starts teaching him how to fly a real kite. He gets up and rides his first day. Must be the teacher.

Pat Bordner is one of Jon’s kite buddies from Florida, and it’s a riot watching him take the worst wipeouts trying to learn an S-bend. The guy goes for it full blast and destroys himself. He finally gets it and is sticking them clean, but he’s bruised and beaten by day’s end.

It’s a magical day because someone gets his first taste of the sport we all love, and it’s also a day for new friends to live life to the fullest, even though we do have the occasional carnage. We get off the water and head to Greenport by boat for dinner at a seafood restaurant called Claudio’s with Jon’s dad, uncle and cousins. The atmosphere is incredible and the food outstanding, but we’ve all had one of those days where you’re so tired and hungry you could eat dirt.

The trip would not be complete without a cutthroat croquet tournament. All the boys, plus a few neighbours, jump into a 10-man croquet war exercise. I talk Jon’s brother, Charlie, into watching my back since they’re all gunning for me, knocking the enemy’s balls into the bushes as I make a run for the finish. I get caught with one shot to go, and give up the crown to Pat, the rugby player. I run inside to get some water and return to find Charlie writhing in pain on the ground after being body-slammed by T.J. for his role in my almost-championship croquet week. Everyone’s messing around, but we’re glad to see the U.S. sailing Olympic athlete walk off the lawn without injury.

After a week of unbelievable conditions, it’s time to go home. It’s great living life without a care and creating memories of a place the kiting world knows little of. Long Island is truly a unique resource. The landscape looks nothing like the New York you see on TV; it looks closer to the picture on a Ben & Jerry’s ice cream container: grassy farmland with cows and a red barn. With plenty of summer sun, warm water and great scenery, it can’t be beat for flatwater kiting and “good breeze.”

Local Knowledge

Location: Shelter Island, New York
Closest airport: MacArthur Airport, New York
When to go: June to October
Water temperature: Summertime you can ride in baggies; otherwise, you’d better be a polar bear
Other places to ride: Any beach along southern Long Island
Gear choice: Medium to big kites; mostly flat water
Beer and food: Expensive, but plenty of it. Try Primo Pizza on Shelter Island


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