For my family, summer is the paragon of our existence. My wife, Jen, who is a social worker in the largest school system in the country, gets the unbroken break she needs from her demanding career. Class is also out for our teenage daughter, and my adult son and his girlfriend visit often. The season also coincides with a respite in business travel for me that picks up in intensity during the fall boat show season and seemingly doesn’t stop until the next summer solstice.
This past summer, we took full advantage. We spent what seemed like days swimming in the ocean. We went to outdoor concerts and accepted every invitation to visit friends with beach houses. Barbecues and dining alfresco on the bounty of summer produce was a salutary bookend to long days spent outside.
Right in the middle of our summer, there was a weekend that encompassed the best of the season. Of course, it began and ended on the water.
It started with a day on the beach and boardwalk in Asbury Park, New Jersey. I then rallied my crew with late-afternoon, thin-crust pizza and a weather report that showed an escape route from the heat wave. It was at the end of Long Island, New York.
Three hours later, caffeinated and a bit delirious from the seasonal squeeze on the expressway, we pulled into the village of Greenport, New York. Flanked by the Long Island Sound and Gardiners Bay, Greenport is a popular destination for boaters, with a small-town charm and a sterling reputation as a dining destination that is surrounded by verdant vineyards.
We took up residence in a hotel along the village’s restaurant- and boutique-laden main drag, and we began our North Fork adventure a short time later on a friend’s Grand Banks 47 Classic. While the kids were off looking for good-natured trouble, Jen and I toasted the boat’s owner with Sancerre. We watched the weekly concert series at Mitchell Park from the 47’s comfortable flybridge.
The next morning as everyone slept, I snuck out with my bike. Sometime later, I was racing the ospreys along the bay at Orient Beach State Park. The preserve, a maritime forest with red cedar and prickly-pear cactus, is edged by “old” Long Island—oyster farms, vast potato fields that stretch to the water’s edge, and cedar-clad homes with long, two-track driveways. I yielded to a tiny diamondback terrapin before rounding Orient Point and heading back, stopping to pick up lattes for my sleepy crew.
We spent the next two days in bathing suits, and it was magical. When we weren’t towing the kids around behind our extended family’s runabout, we were swimming off Shelter Island in Gardiners Bay. We dropped anchor, ate lunch and struck up a conversation with the other gunkholers, charming our way onto a Back Cove 39O for late-afternoon oysters and a refreshing sauvignon blanc. Both the bivalves and the wine were sourced within a few miles of our anchorage.
The last night ended, of course, how each day should properly end: with loved ones on the brine. As the sun set somewhere over Long Island Sound, I floated in the salt water and watched the darkness rise, only swimming back to the boat when my family said we’d be late for dinner.
This article originally appeared in the October 2025 issue of Passagemaker magazine.
