A vessel with “Sail Haven” printed on its slender triangular sail is crossing New Haven Harbor. Instructor Eric Greenberg stands on the aft deck and addresses five sailors-in-training, who are variously poised at a long lever that controls the rudder, a line that orients the jib and a swinging boom that angles the main sail. “See how the sail is flapping and it means we’re luffing? That means we’re straight into the wind. So to get out of the wind, we want to point that way. So, Milagros, steer us that way.”
The boat, a 19-foot Flying Scot, is now moving decisively in the direction of Gateway Terminal in the Port of New Haven. Having drifted straight into a stiff breeze coming from Fort Hale, it had briefly, in the poetical parlance of the boating world, been “in irons,” losing speed while its sail rippled noncommittally behind the mast. But when the tiller is pulled at Greenberg’s instruction, the boat turns, and the sail bows, stretches and swings out over the water while three students on the port side duck to let it pass. “Nice! Perfect!”
“The way sailing works,” Greenberg explains, “is we’re redirecting the wind to push us because, you know, equal and opposite reaction. So if the wind is going that way, it’s gonna push us that way.” He points broadly starboard, then to the bow. At a near 45-degree angle to the breeze, the sail is now directing the boat in the direction the boat is actually pointed.
The wind-powered voyage feels quiet and calm, the only sound of combustion coming from late-day traffic on the interstate behind us. But as we approach and then pass the orange buoy that signals the time to turn, it becomes apparent how fast the boat is going. The sail flaps as if it were alive, not merely harnessing but also expressing the wind’s power. Under its sway, you realize how sailing can become an obsession, or at least an absorbing hobby, long after its late-19th-century supplantation by the steam engine.
Making sailing accessible is the mission of Sail Haven, which joined what’s now called New Haven Community Boating, based at the Canal Dock Boathouse, in 2023. Regular membership, which currently costs $295 annually (with financial assistance available for those who qualify), buys you and your guests recreational boating privileges using Sail Haven’s fleet, with formal instruction available for an additional $280. “The idea was: How can we bring the sport that we love to as many people as possible?” explains Steve Machesney, chair of the Sail Haven steering committee. “A lot of folks don’t think of sailing as being accessible, and they’re right. The cost of entry is high. Belonging to a yacht club has a cost and it’s high. [The cost of] owning a boat and maintaining a boat is high. Our goal was to remove all those things and to make it as accessible as possible.”
And New Haven Harbor turns out to be an ideal place to do it. Before I get on the boat, Machesney reintroduces me to it. He points to a yellow buoy, visible in front of the giant storage drums across the harbor. “That’s the edge of the shipping lane. We got to stay out of there… Ships like that tugboat”—a squat vessel making grim progress toward the Tomlinson and Q Bridges—“especially if it’s towing something or pushing something, it can’t stop. So we got to stay out of the way.” Machesney compares it to the harbor’s near edge, pointing toward Long Wharf Pier on our right. “It’s just crazy shallow, so you see gulls standing in it a ways out, especially at low tide.” Between the deep industrial channel and the mud flats—and backed by a clear yet invisible border from Black Rock Fort on the east shore to Sandy Point in West Haven—is a tidally consistent, optimally deep 1.5-mile arena for recreational boats.
At that moment, Sail Haven boaters are racing in the middle of it. “There’s no scorekeeping. There’s no ranking. There’s no trophy,” Machesney explains. “It’s getting people who are newer to sailing used to the concept of racing.” In the pageant of sails, Machesney makes out some of the highlights. “This one here going pretty fast compared to the other ones. That’s a 420. The one up there is a Laser”—two boats built for speed, among the six different models that make up the Sail Haven fleet. “And then you also have the Sunfish scattered in there.” The Sunfish is said to be the most approachable, no longer than a kayak, with one sail and one line to control it.
It’s a testament to the subtle and unsubtle variations in those boats that the same wind is powering all of them. The wind is the first condition of the harbor to announce itself on any given sailing day. “It can be dead calm in Westville, for example,” says Machesney. “But the way that the harbor is situated, I go down to the platform, and it will be blowing 10 knots out of the south.”
“It always blows from the southwest or the northeast,” Greenberg adds an hour later from his perch on the Flying Scot’s aft deck. He then indicates all the other directions it could be blowing from. “I’ve never had it come from that way. Never from that way. Never from that way. Always there. It’s weird.”
Its consistency is good for lesson planning. Greenberg has taken his students out on a “hot dog course”—so named (presumably) because the boat, if guided correctly around two alternating buoys, traces the outline of a hot dog. “So we have the [course] set up perpendicular to the wind. We’re going to go around it on a beam reach,” where the wind blows sideways across the boat. “And then we’re going to do one at the jibe”—a downwind turn accomplished by shifting the side of the sail that’s capturing the air—“because you’re going with the wind, and then a tack”—doing the same basic thing upwind—“because you’re going through the wind. Nice and easy.” Jibing and tacking are the very stuff of sailing. If you can do both, you can make the boat go—or make the wind make the boat go—exactly where you want it to, and then you’re off to the races.
Greenberg is now tracking the diagonal approach of the buoy. “Okay, we’re going around it. We’re gonna be on the right. So straighten it out. Nice job, Aish. And then we’re gonna keep going until it’s past us, and then you’re gonna jam the rudder all the way behind you.” This begins a series of actions that move roughly from stern to bow. The tillerperson and the mainsail swap sides—one sidestepping, the other rotating. Trainees seated midship stand to guide the boom. Greenberg turns his attention to the jib, the small sail on the foredeck. “So Dee? Luke? Wait for when the sails begin to luff in the middle. As soon as we start tacking, un-cleat. That way, it can luff freely.” The boat continues to turn. The line that orients the jib is freed. “Then, when it starts luffing, that’s when you pull it to the other side.” The jib flutters hopefully, prompting a two-sailor operation, one letting the line out on one side, the other pulling the line in. The jib fills up. The boat glides back toward Long Wharf.
Machesney says there are 220 sailors in Sail Haven, a turnout the Sail Haven teams hopes to turn into a community. “When you come down and you don’t really know how to rig a boat—you’re doing it for the first time—you can ask another member to help you and they’re gonna say yes. They’re gonna help you. Or a dockmaster’s gonna help you. Or if you are down by yourself for the day and some people are going out in a Flying Scot, you’re like, ‘Hey can I tag along?’ They’re gonna say, ‘Sure!’ Because they want that to happen.”
What Machesney describes is not only a community but a scene, one that starts on the boathouse platform, and spills out—or tacks or jibes out—into the harbor. A green flag waves from the platform to signal good conditions. The dockmaster discusses needs and capabilities with each member as they put on their life jackets, and the harbor gradually fills with boats. The staff keeps an eye out. “We do regular scans with binoculars and then we’ll also get out and launch and do regular harbor patrols and keep an eye on everybody,” Machesney explains. “In a one and a half-mile radius, that’s doable.”
More experienced sailors, with the dockmaster’s permission, may go three miles out, to the outer harbor. The larger boats—the “daysailers”—are thus equipped with VHF radios. Joel Zackin, one of the founders of Sail Haven, sums up one of the variables that can become more variable the further you go out. “Sailing in a very, very light wind like this is difficult. Medium breeze is easiest. Higher winds, everything happens faster with more force.” The force of a wind that has suddenly gone from 10 knots to 30 can capsize a boat.
But it’s one thing to know all that, and another thing to experience it. “The boat and the wind and the sail—they teach you,” Zackin says. “You may not realize it at the time. The more you sail, the better you become.” And the more people it puts under sail, the better Sail Haven presumably becomes. “Yeah, you could read about sailing. Someone could talk you through it. But you just got to do it,” Machesney says. “We really just want to get people on the water so they can do it.”
Written by David Zukowski. Images 1 and 4, featuring scenes from a recent open house event, photographed by Jessy Trujillo and provided courtesy of New Haven Community Boating. Images 2 and 3 photographed by David Zukowski.
