Doug Ryan

There’s something quietly powerful about a 25-foot boat. She doesn’t dominate the marina or make your dock neighbors jealous — but she’ll take you just as far, maybe even farther, because she’s yours. In a world where boat shows keep getting flashier and every glossy ad seems to feature a 50-footer with twin helms and … Read more

If you’ve spent any time around a marina, you know that sailors love to argue about which boat is the “best.” But when we talk about the most influential and beloved sailboats ever made in North America, the debate gets a little easier. From dinghies that launched a million sailors to ocean-crossing cruisers that changed … Read more

If you’ve spent any time in a marina or wandered through a used-boat listing, chances are you’ve seen a C&C. For decades, these Canadian-built yachts were the gold standard of racer-cruisers—boats that could take line honors on Saturday and still carry the family on a comfortable Sunday sail. From their early dominance on the racecourse … Read more

Not every boat that’s ever splashed into American waters was a masterpiece of naval architecture. For every timeless design like a J/24 or Catalina 30, there were clunkers that left their owners swearing off sailing altogether. During the big fiberglass boom from the 1960s through the 1990s, manufacturers churned out hundreds of models in the … Read more

If you’ve ever daydreamed about trading your daily commute for a mainsail and a horizon, you’re in good company. Chartering a sailboat is one of the easiest ways to taste the cruising life without the long-term commitment (or the boatyard bills). Over the years, I’ve sailed in some incredible places, and I’ve also spent way … Read more

There’s something about sailboats that just begs to be captured on film. The crashing waves, the creaking rigging, the human drama of being surrounded by nothing but sea and sky — sailing is tailor-made for the big screen. Luckily for us, filmmakers have been turning out some truly memorable sailing movies since the 1980s. Some … Read more

If you were anywhere near a yacht club, beach, or lake in the 1970s through the 1990s, you knew these boats. They were fast, fun, accessible, and—most importantly—raced in fleets big enough to make every start line a heart-pounding moment. Some are still going strong, others have faded into cult-classic status, but all of them … Read more

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 … Read more

If you learned to sail in the 1970s, 80s, or 90s, chances are good you either owned—or at least sailed on—a Hunter. For decades, Hunter Marine was the go-to American sailboat builder for families who wanted to get out on the water without selling the house or taking out a second mortgage. Hunters weren’t always … Read more