Sailing Sag Harbor’s Waterways into the Cooler Months

The double-masted catamaran Heron is one of two US Coast Guard Inspected Vessels in the Sag Harbor fleet.

First, there’s Lelanta, the original pride of the Sag Harbor charter fleet under captain Dave Brown — an undeniably stunning vessel with perfectly varnished wood that makes it the go-to sailboat for overnight adventures.

Then, there’s Valkyrie Sailing Charters with captain Paul Norris, an Australian who looked a bit like a mountain man until he came back this year with trimmed hair and a shaved beard, a transformation that no one recognized — from captain Graham Godsall of Dove Sailing Charters, the perfect picture of an English captain with endless sailing stories, to Sea Escapes captain Erik Skilbred, the warm, well-mannered youngster among a sea of salty veterans.

There’s captain Shannon McLellan, sweet and bubbly with an eye for hospitality that sets Heron Yacht Charters apart, making it the busiest charter in New York State and, along with the time capsule American Beauty, one of two US Coast Guard Inspected Vessels in the Sag Harbor fleet.

This is just a taste of the close-knit Sag Harbor charter scene, but a significant one, as these boats have one thing in common: they all stick around for the fall sailing season.

“People associate sailing with summer and they assume all the boats have left, because a lot of the boats leave after Labor Day,” McLellan said. “But there are quite a few of us still here.”

Wool socks insulated with hot rocks await passengers on Heron during the cool fall season.

The sailing season, which begins in May, can stretch all the way into October, weather allowing, McLellan said. Some of the charters lengthen their routes — the water is still warm this time of year, Skilbred notes — while others change their course altogether, including Heron.

“Usually, we head straight for a swim spot, but this time of year, we’re not doing that so much, so it’s more of a relaxed itinerary,” McLellan explained. “It’s a little chilly, so the biggest change for us is the menu. We go from having lobster rolls to lamb chops, and we have this beautiful tea menu from Plain T in Southampton.”

On any given Heron charter, guests can find a basket of fluffy white blankets spritzed with lavender on the bow, 20 pairs of wool socks insulated with hot rocks, and a spotless interior dotted by at least four bunches of white hydrangeas, white orchids and two dozen white roses, McLellan said.

“We always say, service first, sail second. We always want that wow factor,” she said. “It’s a beautiful little micro-universe — just us and the water.”

Since moving from where she started in Montauk, she has grown to have a family in Sag Harbor — unable to help herself from smiling as she gets caught up in Captain Graham’s stories, or listening to American Beauty backing out of the harbor.

“Don’s got this tour recording playing; I’m pretty sure it’s a cassette, it’s gotta be,” she said. “You’ve seen the boat, it’s probably been there longer than I’ve been alive. I love it, it’s adorable. And he’s awesome. It’s a Sag Harbor experience.”

Captain Eric Skilbred is the newest, and youngest, captain in the fleet. At just 35 years old, the Sag Harbor native helms Sea Escapes, which offers half- and full-day sails, as well as sunset tours, which sometimes incorporate his expertise as a windsurfing and paddle-boarding instructor.

Passengers aboard the American Beauty.

He says he wasn’t nervous to come on the scene, and told the other captains he didn’t want to step on any toes. He immediately felt welcomed, he said, though it didn’t hurt being a local.

“It was my dream, to start a charter company. Being out and sailing, it’s one of the more freeing things you can do for yourself and your time,” he said. “It’s therapeutic. You’re only focused on sailing, you’re not worrying about the other stuff in life.

“The fall season is the best time of year, I’m totally convinced of that,” he continued. “I’m really happy to be out on the water with these guys, and I’m happy to be living in Sag Harbor.”