I've been getting into sailing, solely for the purpose of cruising and sailing for fun with no interest in racing. As I've started talking to sailors, I've realized that you need to gauge whether you're speaking with a racer or a cruiser. Racers will claim these are not mutually exclusive categories, because of course racers can also cruise. But racers who cruise will ultimately talk to you like racers.

Racers are, as you might expect, fanatical about performance. They will go very deep into details about optimizing sail trim and shape, and using wildly-named specialized foresails (not merely spinnakers, but asymmetric spinnakers, reachers, screachers, code-zeroes, etc). It's a bit like talking to an SCCA racer about your new pickup truck.

In fact, if you have a good grounding in the basics of sail trim ("when in doubt, let it out"), and know how to put a reef in you can have a fine time getting between points A and B in a sloop with a basic mainsail and jib.

I learned to race first and am now learning to cruise. And I’m glad I learned in that order. Cruising has a very specific set of skills that you’ll never learn racing. That stuff will be obvious and if you want to cruise, you’ll learn those skills.

But what is not obvious to cruisers is that racing teaches you how to handle your boat in many different and difficult conditions, with confidence. When you race you have to go from a specific place to another specific place and you don’t get to pick the weather. You’re often pushing your boat and are in high stress situations.

Often, cruisers will go out, when it’s nice, and turn on the motor when they can’t make their boat go the way they want it to go.

So, what happens when you’re out sailing and an unexpected storm rolls in? Because if you sail enough, especially offshore, it 100% without a doubt will happen. I’d honestly be pretty comfortable handling the boat through all but the worst weather, boat breaking weather. And even that, I would be confident in my safety gear and ability to contact support for a rescue. Because all of that is drilled into you as a seasoned racer. And I’ve been through some bad weather on the race course. I’ve had to make my boat go upwind in horrible sea state for hours on end while my crew is throwing up from sea sickness.

There are multiple occasions on which I’ve turned down sailing with cruisers because I just don’t trust that they have the skills or equipment to keep me safe should things go sideways.

Exactly right. I’ve known from when I started sailing 35 years ago that I was a racer.

Sailboat racing is amazing; it’s this incredibly complex exercise involving physical boat handling skills, teamwork, leadership, communication (in a jargon that itself takes a year to internalize), as well as physics, geometry, meteorology, and minute observation of effects (that dark patch on the water or the flutter of a telltale). All of this feeds into strategic decisions on where to position your boat and tactical decisions of how to do so.

It looks crazy boring from the outside but if you get into it, it’s an activity that is intensely mental as well as physical and requires a very broad set of skills.

I finished my first race Wednesday after a few years sailing casually. And, although it’s true that whenever there is more than one sailboat going the same direction it’s a race, being in a fleet on a defined course is much faster paced and precise. My analogy to driving is that cruising is being able to drive on empty roads, and racing is driving in traffic — it becomes about understanding the flow and rules spoken and unspoken.

I've been seeing some modern junk rig refits on the great lakes the last few years, which really gives me hope about dedicated "get there when we get there" sailors. Those things are basically optimized for chilling the fuck out. Easy to sail (entire tacking maneuver is basically just throw the rudder over and duck), easy to reef, don't heel as hard, straightforward to mend the sail or running rigging on the fly.

Only downside is their close haul is like 12º off the wind vs a bermuda rig and no one knows how to make them. The east coast (esp chesapeake) has some traditional gaff rig setups that have similar tradeoffs, like catboats. I would love to see more small production boats target this end of the "speed/comfort/cost" triangle. Currently it's like if the only bicycles available were race-ready track bikes. But sailing is already a small niche and new boats even smaller I think.

There's also a specific argument in selling the racing is a better way to develop sailing skills because cruising ideally may not challenge you.

Spot on. As a racer, I can say this is mostly true. Although for me and many of the other racers I know, it's less about going deep into the optimization, sail choices, etc, and more about just being competitive. Racers don't always make good cruisers because they're always trying to go faster and push harder, whereas most cruisers want to slow down and enjoy the journey.

If there's more than one sailboat, it's a race :)

Isn't that the case with every hobby?

I was born into sailing though dad, and I know how he is about performance and ekking every little bit out of what he can (and can afford) (no huge stuff, 21ft). I mean I never let the sails go all out of trim, but I can appreciate putting it on good enough, setting the autopilot and just chill and listen to the sound of sailing, the sound of sailing in a mild summer day is peak life

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