When people argue about the “best” sailboat, they usually mean their sailboat.But popularity is different. Popularity is measurable. The boats on this list earned their place not through marketing or prestige, but through sheer adoption. They were bought by regular people. They were sailed hard, sailed badly, sailed everywhere—and then sold to the next generation … Read more

For years, sailors have been asking the wrong question. The question isn’t “Why don’t people sail anymore?”The real question is “Why would they?” For much of the public, sailing looks expensive, intimidating, and locked behind gates—both literal and cultural. Boats cost money. Time costs money. Marinas feel exclusive. Yacht clubs feel like you need an … Read more

Because Not Every Boat Was Blessed With Good Looks Beauty may be in the eye of the beholder—but let’s be honest, some sailboats push that theory to its breaking point. Over the years, designers have chased interior space, cost savings, performance, innovation, or pure ego, and sometimes the looks were the first thing tossed overboard. … Read more

If you believe sailing is expensive, you didn’t come up with that idea on your own. It came from: Modern sailing media rarely shows the truth: Because none of that sells new boats. What does sell is the idea that sailing requires money, upgrades, and constant spending. And once that idea takes hold, people assume … Read more

Let’s have a little heart-to-heart about something that’s becoming more and more common out on the water: sailors – especially newer ones – relying too much on their tech and not enough on their instincts. And I get it. Today’s boats are floating computers. You’ve got autopilots that steer better than most humans, chartplotters that … Read more

How Owners of 1970s–80s Cruising Sailboats (25–45 Feet) Can Get the Most Bang for Their Buck If you sail the U.S. or Canadian coasts (or the Great Lakes), you already know one hard truth: the best deal in boating today is a well-maintained older fiberglass cruiser.Catalina, Pearson, O’Day, C&C, Hunter, Tanzer, Cal, Newport—these boats were … Read more

Sailing Back in Style There’s something magical about seeing a classic-looking sailboat gliding silently across the water. It’s not just nostalgia—it’s a full-blown comeback. All across the U.S. and Canada, sailors are falling in love with boats that look like they belong in a Hemingway novel but sail like a Tesla. Whether it’s brand-new designs … Read more

Hooked on Sailing, but Not on Debt? Thinking about getting into sailing but not ready to sell your car, house, and dog to buy a new boat? You’re in good company. For new sailors in the U.S. and Canada, a 40-year-old sailboat between 25 and 45 feet might be the ticket to life on the … Read more

There’s a friendly battle raging at marinas and yacht clubs: classic boats vs. modern boats. Ever heard an old-timer grumble, “They just don’t make ’em like they used to,” while patting the teak rail of a 1975 sloop? Or a tech-savvy sailor brag about their brand-new boat’s push-button sails and high-speed hull? 🌊 The debate … Read more