10 Things I Wish I Knew Before Buying My First Sailboat

Buying your first sailboat feels a lot like falling in love — thrilling, impulsive, and occasionally expensive. Looking back now, I wish someone had handed me a salty cheat sheet before I handed over the check. So here it is: ten things I wish I knew before buying my first boat, written for anyone in … Read more

The Great Debate: Is Powerboating Really Easier?

Walk down any dock in the U.S. or Canada, and you’ll hear it: “Powerboating’s easier!”“Sailing’s real boating!” The debate has been going on for decades — loud, friendly, and fueled by equal parts pride and rum punch. So, is powerboating actually easier, or are sailors just making it look hard on purpose? Let’s hoist the … Read more

20 Things Only Sailors Understand (and Powerboaters Never Will)

If you’ve ever tried to explain sailing to a powerboater and watched their eyes glaze over halfway through “weather helm,” you’re not alone. Sailors and powerboaters may share the same waters, but we live in completely different universes. Sailing isn’t just transportation — it’s a mindset, a lifestyle, and occasionally, a form of group therapy. … Read more

The Magic of Small Boats: Why 25 Feet Is All You Really Need

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

The 10 Best Sailboats of All Time (Built in the U.S. & Canada)

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

C&C Sailboats: The Rise, Glory, and Fall of a Racer-Cruiser Legend

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

The 10 Worst Sailboats Ever Sold in the U.S.

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