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Captain Paul Kreiling and first mate James Lockley of Easterly Sailing. (Credit: David Benthal)

There’s always a bittersweet note to the month of August. If you’re anything like me, the month arrives and you begin to lament how the summer has flown by; how you didn’t make it to the beach nearly enough.

Of course, the actual end of summer is well into September. There are still hours and hours of daylight to enjoy swimming in the bay, plucking ripe peaches from their branches, and perhaps taking an afternoon sail.

It’s the perfect time of year to enjoy the North Fork from the sea.

Late-summer afternoons make for ideal sailing conditions: still-warm days, balmy evenings and a more laid back setting to stretch the season to last just a little bit longer.

At Easterly Sailing, a yacht charter based out of Safe Harbor in Greenport, you aren’t just invited aboard to enjoy the graceful Peconic Bay, but to immerse yourself in all of the adventure sailing offers.

“We are not the sit and sip wine sail. We want you to participate,” explains Captain Paul Kreiling as he welcomes me aboard the Yikes, his nimble, 33-foot J/100 sloop.

Captain Paul Kreiling. (Credit: David Benthal)

“She’s a dream to sail. You’ll try it out,” Kreiling continues.

Wait, what? Me? My eyes widen, partly at the name of his boat, partly at his invitation. I give up my secret: this is my first time on a sailboat, ever.

Kreiling and his gentle, soft spoken first mate, James Lockley, quickly alleviate any fear or hesitation on my end. Soon enough, the motor roars to life and we’re heading out of Stirling Basin. 

He and Lockley begin communicating as his first mate pulls at the halyard and the mainsail starts to unfurl, flapping in the wind.

While this happens, Kreiling talks through the basics: sailing 101. He points to an arrow on the top of the mast, explaining that everything is affected by wind. “Not to be sacrilegious, but we call that God,” he said. “Everything is dependent on the wind.”

We’ve just made it into the bay when he cuts the engine off and a sense of peace washes over us. I close my eyes and feel the gentle undulation of the water, hear a seagull call overhead as salty bay water sloshes the side of the hull.

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

On a two or three-hour charter, you’ll be glad to be with Kreiling. As we glide through the water on aseemingly perfect summer day, he explains that he’s been navigating these waters since he was a kid growing up in Mattituck. As many local kids do, he left for 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 courses in graphic design 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 at the East End Seaport Museum & Marine Foundation.

All of this to say that Kreiling has a uniquely local perspective, from the history of the village — known in pre-Revolutionary times as Stirling and then Greenhill — to pointing out that many of the condominiums and other developments along the shoreline today used to be mostly working shipyards and oyster factories. His deep love for the area is evident. He can take you to the best swimming spots, to the best birding spots and recommends his favorite restaurants to guests before they disembark. “These are the little things that I get to impart,” he said.

In the last few years, Kreiling said he’s also noticed the water quality begin to improve. 

“The fish stock is replenishing, the water is actually clearer. The red tides don’t seem to be as prevalent as they were,” he said. In turn, this has allowed for more wildlife sightings of 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 the North Fork after he retired in 2015.

“I don’t take this for granted,” Lockley said. He spent much of his career living on the west coast and when he moved back to Long Island, didn’t expect to be working 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 can’t recall exactly how they met, but are certain of one thing: they were both crewing for the Peconic Bay Sailing Association at the time. “We’ve just always been friends,” Kreiling said.

Since launching Easterly Sailing 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 along towards Shelter Island, I’m told to pick out a fixed point on the horizon and aim for that direction. Maneuvering the tiller is tricky at first, since the boat moves in the opposite direction of the way you turn it.

Soon enough, I get the hang of keeping her on a straight course and we’re cruising along at 8 knots. 

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

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

It’s a freeing feeling, being propelled by the elements. And only slightly terrifying when the boat begins to heel, tilting as the wind moves through the sails.

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

That both Kreiling and Lockley have sailed all over the world and are still enamored by eastern Long Island waters is worth noting.

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

We sail past Shelter Island’s Sunset Beach and explore Pipes Cove before turning to head back to the marina. To my surprise, two hours have passed.

On our way back, Kreiling points to a patchy, dark gray cloud in the horizon. A pop up summer storm. This, he explains, is just another thing to look out for in addition to swirling tides, changing winds, buoys and other boats.

During charter excursions, he passes on this knowledge. It applies to life on land, too.

“I’ve found that when people are experiencing a little sea … discomfort, you let them drive,” Kreiling said. “Then, they’re not looking 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 well into October. For booking and availability, visit, call or text 631-495-0216.