Channel your sense of adventure with Easterly Sailing


There is always a bittersweet note to the month of August. If you’re anything like me, the month arrives and you begin to lament the passing of summer; how you didn’t get to the beach enough.

Of course, the real end of summer is September. There are still hours and hours of daylight to enjoy swimming in the bay, picking ripe peaches from their branches and perhaps going for an afternoon sail.

This is the perfect time of year to enjoy the North Fork from the sea.

Late summer afternoons offer ideal sailing conditions: still warm days, mild evenings and a more relaxed setting to extend the season a little.

At Easterly Sailing, a yacht charter based in Safe Harbor in Greenport, you are not only invited aboard to enjoy the graceful Peconic Bay, but to immerse yourself in all the adventure sailing offers.

“We’re not sailing wine sitting and sipping. We want you to participate,” says Captain Paul Kreiling as he welcomes me aboard the Yikes, his nimble 33-foot J/100 sloop.

Captain Paul Kreiling. (Credit: David Benthal)

“It’s a dream to sail. You will try it,” Kreiling continues.

Wait what? Me? My eyes widen, partly at the name of his boat, partly at his invitation. I reveal my secret: it’s the first time I’ve been on a sailboat, ever.

Kreiling and his sweet, gentle first mate, James Lockley, quickly quell any fear or hesitation on my part. Soon the engine roars and we leave Stirling Basin.

He and Lockley begin to communicate as his mate pulls on the halyard and the mainsail begins to unfurl, flapping in the wind.

As this happens, Kreiling talks about the basics: sailing 101. He points an arrow to the top of the mast, explaining that everything is affected by the wind. “It’s not sacrilege, but we call it God,” he said. “It all depends on the wind.”

We have just arrived in the bay when he cuts the engine and a feeling of peace comes over us. I close my eyes and feel the gentle ripple of the water, I hear a seagull call overhead as the salt water of the bay laps against the side of the hull.

“That’s why you sail,” Kreiling said. “Because it’s quiet.”

On a two or three hour charter you will be happy to be with Kreiling. As we glide across the water on a seemingly perfect summer day, he explains that he’s been cruising these waters since he was a kid growing up in Mattituck. Like many local kids, he moved to Manhattan, developed a career in advertising and graphic design, and returned to put down roots and start his family in Greenport in the early 90s. He taught graphic design classes and photography at Southold High School, worked as a sailboat specialist when Safe Harbor was still Brewer’s, is a longtime sailing instructor and current chairman of the East End Seaport Museum & Marine Foundation.

All this to say that Kreiling has a unique local perspective, from the history of the village – known in pre-revolutionary times as Stirling and then Greenhill – to point out that many condominiums and other developments along the shoreline were today formerly mainly shipyards and oyster factories. His deep love for the region is evident. He can take you to the best swimming spots, the best birding spots, and recommend his favorite restaurants to guests before they disembark. “It’s the little things that I can pass on,” he said.

Over the past few years, Kreiling said he’s also noticed the water quality starting to improve.

“The fish stock is recovering, the water is actually clearer. Red tides don’t seem to be as prevalent as they used to be,” he said. see more dolphins and seals in local waters.

Lockley, a retired naval officer and navigator, grew up in South Merrick and spent many summers sailing and racing in New Suffolk. He moved to North Fork after retiring in 2015.

“I don’t take that for granted,” Lockley said. He spent much of his career living on the West Coast and when he returned to Long Island he never expected to work on the water again. “The North Fork is a beautiful place,” he said. “Once you get out on the water, you get a different perspective.”

First Mate James Lockley. (Credit: David Benthal)

The two don’t remember exactly how they met, but are certain of one thing: they were both crew members of the Peconic Bay Sailing Association at the time. “We’ve always been friends,” Kreiling said.

Ever since Easterly Sailing launched in 2012, they knew they wanted to share the adventurous spirit and hands-on experience with others.

“Anyone can learn to sail,” Kreiling said.

Now it was my turn for a (very) basic lesson.

As we glide towards Shelter Island, I am told to pick a fixed point on the horizon and aim in that direction. The tiller maneuver is tricky at first, as the boat moves in the opposite direction to which you turn it.

Soon, I decide to keep it on a straight course and we are sailing at 8 knots.

“Look where you’re going and feel it. And try not to aim at the ferries,” Kreiling said. “I’ve been sailing here for a long time and most ferry captains know me.

“And if they don’t know you,” Lockley adds, “they have a very convincing horn.”

It’s a feeling of liberation, being propelled by the elements. And only mildly terrifying when the boat begins to heel, heeling over as the wind shifts through the sails.

Two years of pandemic life hasn’t exactly presented a ton of opportunities to get out there, be brave, and try something new. The sailing lesson was the perfect reminder that there are adventures waiting for you even in your own backyard.

It should be noted that Kreiling and Lockley have sailed all over the world and are still in love with the waters off eastern Long Island.

“There are a lot of wonderful places on the planet to sail,” Lockley said. “One of the things that sticks with me here is the deep water and the little coves…there’s so much diversity.”

We sail past Sunset Beach on Shelter Island and explore Pipes Cove before returning to the marina. To my surprise, two hours have passed.

On the way back, Kreiling points to an uneven dark gray cloud on the horizon. A pop-up summer storm. This, he explains, is just another thing to watch out for besides swirling tides, shifting winds, buoys and other boats.

During charter excursions, he transmits this knowledge. This also applies to life on earth.

“I’ve found that when people feel a little sea…uncomfortable, you let them drive,” Kreiling said. “So they don’t look down thinking how miserable they are. You have to look ahead. »

Easterly Sailing offers two- and three-hour charters for up to six people, sunset sails and sailing lessons through October. For booking and availability, visit, call or text 631-495-0216.


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