Sailing students make their way around Port Jefferson Harbor during...

Sailing students make their way around Port Jefferson Harbor during a class offered by the sailing school at the Port Jefferson Yacht Club. Credit: Port Jefferson Yacht Club

After moving to Long Island three years ago, Benjamin Sklar said he wanted to get out on the water, and sailing was at the top of his bucket list. His wife surprised him with five sailing lessons, he said — and he is now hooked.

“I had the time of my life,” Sklar, 31, of Center Moriches, said. “It was a really great experience.”

Sklar said he can now handle a sailboat by himself. He rents when he can, but his goal is to eventually buy a boat of his own.

If you, too, have dreams of sailing away, Long Island has many schools where you can learn the ropes — literally.

Sailing schools typically offer private lessons or small group sessions for adults. Although instruction techniques may differ for each program, you should expect to learn fundamentals like basic sailing theory (how boats sail), steering and navigation, proper terminology, safety procedures and boat handling.

“I don’t think sailing is inherently difficult to learn,” said Luke Hickling, founder and instructor at Moriches Island Sailing in East Moriches. “We go over safety measures first, because if you don’t feel safe you’re not going to enjoy yourself. Once we review the essentials, including controlling the jib and tacking, we move on to docking, anchoring and so on. Wind awareness is probably one of the more challenging concepts to grasp.”

But Will Bradshaw, director of the Port Jefferson Yacht Club sailing school, said while a course can teach you how to navigate a sailboat independently, sailing is something you learn over a lifetime. “You never want to get comfortable. You always want to be learning,” he said.

Many beginners want to know how many lessons they’ll need before they’re ready to set sail on their own. “I would say usually after 10 lessons or so people start to feel confident, but it varies for every student,” Bradshaw said.

Ultimately, experience is the best teacher when it comes to sailing: “You can’t control the weather. It’s very unpredictable,” Bradshaw said. “Learning to sail defensively in different situations takes time, just like defensive driving.”

Where to Learn:

Ready to take the plunge? Here are a few options for sailing lessons on Long Island:

Many town recreation programs offer sailing lessons as well. Check your town website for information.

What to Wear:

You’ll be in the sun and on the water, so material that dries quickly and offers SPF protection is ideal. A hat, sunblock and additional layers are also suggested.

When to Go:

Sailing lessons are offered in the spring, summer and into the early part of fall. Keep in mind lessons may be cancelled last minute due to inclement weather.


Group classes can cost as little as $50 per person, with private lessons reaching $250 or more for a single session.

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