O’Day Sailboats: Affordable Adventures and a Legacy That Lives On

If you’ve spent any time poking around small marinas or browsing used sailboats online, chances are you’ve seen the name O’Day more than a few times. Maybe it was on the side of a sun-faded dinghy that’s been teaching kids to sail for decades. Maybe it was on a 22-footer with just enough space for a weekend trip. Or maybe it was on a bigger cruiser with that unmistakable 1980s O’Day styling.

Whatever the case, O’Day boats have a way of showing up. They’re still out there in big numbers, quietly carrying on the dream that their founder, George O’Day, imagined back in the late 1950s: sailing should be for everyone.

The Birth of O’Day

The story of O’Day starts with George O’Day himself — a Harvard-educated sailor who knew a thing or two about boats. In fact, he won an Olympic gold medal in sailing in 1960. But even before that, he had his eyes set on something bigger than racing glory. He wanted to bring sailing to the masses.

In 1958, O’Day founded the O’Day Corporation and teamed up with U.S. Molded Plastics, one of the early pioneers of fiberglass boatbuilding. Fiberglass was the game-changer of the era: cheap, durable, and easier to shape than traditional wood. O’Day saw it as the perfect material for making small, affordable sailboats that a family could tow behind their car and launch on a Saturday afternoon.

The first big hit? The O’Day Daysailer, designed in part by the legendary Uffa Fox. It was small, light, easy to rig, and most importantly — fun. That little boat would go on to sell more than 12,000 units and spark a whole movement of one-design racing fleets that still exist today.

O’Day for Everyone

What set O’Day apart was their commitment to accessibility. While other brands chased performance or high-end cruising, O’Day focused on boats that regular people could buy. They offered:

Dinghies like the O’Day Widgeon, a simple 12-footer that introduced thousands of kids and adults to sailing.
Trailer-sailors like the O’Day 22 and 23, which could be hauled to the lake for the weekend and still provide a couple of bunks for overnight trips.
Pocket cruisers like the O’Day 25, one of their best-selling models, which balanced affordability with just enough comfort for a young family.

By the late 1970s and early 1980s, O’Day was one of the largest sailboat builders in America, rolling thousands of boats out of their Fall River, Massachusetts factory. Walk through a marina in those days and you couldn’t miss them.

The Favorites We Still Talk About

Over the decades, O’Day launched more than 60 different models. Some have faded into obscurity, but others have become true classics. Here are a few that stand out:

O’Day Daysailer (1958) – The boat that started it all. Still raced today, still beloved.
O’Day Widgeon (1960s) – More than 10,000 built, often someone’s very first boat.
O’Day 22 (1972) – A no-nonsense pocket cruiser, trailerable, simple, and tough.
O’Day 23 (1972) – A little more space, a little more comfort — a family weekend favorite.
O’Day 25 (1975) – Hugely popular, with over 2,000 built. Many are still sailing today.
O’Day 34 and 35 (1980s) – Bigger cruisers designed by C. Raymond Hunt & Associates, striking a nice balance between performance and comfort.
O’Day 40 (1986) – The flagship of the line, aimed at serious cruising sailors.

What united all these boats was value. They weren’t flashy, but they were reliable, approachable, and they did the job.

The Beginning of the End

Like so many American sailboat brands, O’Day ran headlong into trouble in the late 1980s.

The sailing boom of the 1960s and 70s was slowing down. Baby boomers who had filled marinas with new boats were aging out of weekend sailing. Powerboats — faster, flashier, and easier to own — started eating up market share. And the U.S. economy was hitting turbulence.

On top of that, O’Day’s corporate parentage got complicated. The company had been sold to Bangor Punta Corporation in the 1960s (the same group that owned Cal and Ranger). Later, it fell under the umbrella of Lear Siegler, and eventually wound up as part of Outboard Marine Corporation (OMC) — best known for Johnson and Evinrude outboards.

By then, O’Day was just a small slice of a much larger business. And when OMC began struggling in the late 1980s, O’Day was one of the first pieces to be cut loose. By 1989–1990, production had stopped. Just like that, one of the great names of American sailboats was gone.

Why O’Day Still Matters

Here’s the funny thing about boats, though: they last. Fiberglass doesn’t just vanish. Even though O’Day as a company folded decades ago, tens of thousands of their boats are still sailing today.

The Daysailer class is still active and vibrant, with racing fleets across the country.
O’Day 22s and 25s are still some of the most common starter cruisers on the used market.
Larger O’Day cruisers from the 1980s remain affordable ways to get into coastal sailing without breaking the bank.

For many sailors, their first taste of freedom on the water came aboard an O’Day. That’s a legacy that’s hard to beat.

Nostalgia, Value, and the O’Day Spirit

When you step aboard an old O’Day, you’re not just stepping onto a boat. You’re stepping into a piece of sailing history — a time when companies believed that anyone could afford to chase the wind.

Sure, O’Day boats don’t have the prestige of a Hinckley or the performance of a J/Boat. But that was never the point. The point was to get families on the water, and in that mission, O’Day absolutely succeeded.

So if you spot a weathered O’Day at your local marina, give it a nod of respect. It might just be someone’s first boat, someone’s dream boat, or the one that quietly kept a whole sailing tradition alive.

George O’Day wanted sailing to belong to everyone. And thanks to the thousands of boats still floating today, it still does.