The Ultimate Guide to Yachting

Gentlemen, let’s talk yachts. Not boats. Not speedboats. Yachts. The floating palaces that scream I’ve arrived—and then immediately offer you a glass of champagne as proof. Yachting isn’t just transportation; it’s a lifestyle, a statement, and let’s be honest, one hell of a conversation starter.

But before you start daydreaming about tossing the anchor off Capri or St. Barts, let’s break it down—because whether you’re looking to charter, buy, or simply know what the hell you’re talking about at a cocktail party, this is your crash course in the world of yachting.

Why Yachting Is the Gentleman’s Sport

Sure, golf is fine, and yes, cigars are still a thing. But yachting? That’s the top-shelf experience. It’s international, exclusive, and ridiculously customizable. You want a party on the French Riviera? Done. A quiet weekend fishing off the coast of Maine? Easy. Hosting your own Monaco Grand Prix afterparty? That’s practically a tradition in yachting circles.

And let’s not pretend it isn’t cool to rub elbows with the men who’ve made yachts part of their personal brands. Think Johnny Depp cruising the Caribbean, Leonardo DiCaprio sunning in St. Tropez, or David Beckham pulling into Miami like Poseidon himself. Even Tiger Woods has a yacht—fittingly called Privacy—because of course he does.

The Events That Matter

If you’re going to claim yacht-guy status, you need to know the international events that keep the scene alive. Here’s your cheat sheet:

• The Monaco Yacht Show (September): The crown jewel of yacht events. Held in the heart of Monte Carlo, it’s basically the Oscars for superyachts. Think billion-dollar vessels, champagne flowing like tap water, and more polished teak than you can imagine.

• The America’s Cup: The oldest international sporting trophy—and still the Formula 1 of sailing. Founded in 1851, it’s all about high-speed racing and billionaire-backed teams showing off their toys. If you ever want to sound cultured at a bar, casually drop a line about Emirates Team New Zealand’s legendary runs.

• The Cannes Yachting Festival (September): Not far from the red carpet, this event mixes the glamour of the film festival with the nautical showrooms of the world’s best shipbuilders. If you want to charter something new, this is your window-shopping paradise.

• Fort Lauderdale International Boat Show (October): The American heavyweight. If Monaco is about sipping rosé with European royalty, Fort Lauderdale is about going big and bold—superyachts, fishing yachts, speed demons—you name it.

Owning vs. Chartering: The Big Decision

Now, unless you’ve got DiCaprio money, owning a yacht might be a bit ambitious. But chartering? That’s the gentleman’s loophole. You get all the bragging rights without the million-dollar maintenance bills (yes, upkeep can run into seven figures annually).

• Owning: You’re in it for the long haul. A status symbol, a tax headache, and a personal floating resort.

• Chartering: You pick the yacht, the crew, the location, and the vibe. Weekend in Ibiza? Easy. Two weeks in the Greek islands? Say no more. Bonus: you don’t have to clean up after the party.

  
  

Dress the Part

Gentlemen, yachting has a uniform. No, not the captain’s hat you buy at a souvenir shop. Think crisp linen shirts, tailored shorts, Tod’s loafers, Persol sunglasses, and maybe a navy blazer if you’re docking somewhere fancy. The vibe? Casual billionaire. Even if your bank account doesn’t quite agree.

The Gentleman’s Takeaway

At its core, yachting is about freedom—the ability to steer your life, quite literally, wherever you want. It’s a blend of power, leisure, and spectacle, wrapped in teak and white leather. Whether you’re following the America’s Cup, booking a charter in the Caribbean, or just dropping yacht trivia into your next poker night, yachting is more than a hobby. It’s the gentleman’s ultimate escape.

So the next time someone brings up golf handicaps or watches, smile knowingly and ask, “Have you ever been to the Monaco Yacht Show?”

Now that’s how you drop anchor in style.