Some while back a nonsailing acquaintance asked me what kind of cruising boat would be suitable for a newbie—something big enough to spend the occasional weekend aboard and to sail within a 10-mile radius of his home harbor. I gave him the stock answer I’ve given many times over the last 20 years—a 23-to-28-foot production boat, cheap, cheerful, easy to look after, and preferably used, so you don’t lose too much on the resale if you discover sailing really isn’t for you. “Sounds awful small,” he said glumly. “Why shouldn’t I get a bigger boat?”

Why not, indeed? The question just confirmed what I’d been thinking for some time—that the starter boat as I once knew it is no more. When I started sailing, it was common to see families of four or more cramming themselves into a 25-footer for a week or two on the water. This was the kind of character-building experience that children put up with only because boats are usually more watertight than tents. You eyed the couple in the smart 40-footer with resigned envy and hoped that one day you too would work up to a boat that size.

Now it’s become increasingly common for totally inexperienced people to point at a well-decked-out 45- or 50-footer and exclaim something like, “I like that one, but does it come in blue?” A short sailing course later, they’re off to cruise around the Caribbean or heading into the Pacific. Seems too easy, doesn’t it?

On the face of it, there’s no real reason why it shouldn’t be. Boats have never been easier to sail or to maneuver under power or to anchor. Electronics have never been smarter; weather forecasts have never been more reliable. Take the right route at the right time of year and there’s not much likelihood of getting your butt kicked. These factors can and do compensate somewhat for a lack of experience, right up until a situation arises that exposes that lack of experience. It’s lucky that for many people, the situation never does arise, or at least not until they’ve amassed the experience to cope with it, if you get my drift. A tight marina, a 3-knot current, and a newbie in a 50-footer used to make for a gratifying spectacle, but bow thrusters have taken a lot of the fun out of it for us onlookers. You still see and hear some horrendous things, though, much like teaching a teenager to drive.

I continue to think it’s a good thing to start low and aim high, if only for the sake of perspective. Once you’ve sampled the claustrophobic confines of a small 1960s cruiser, you’ll never moan about the lack of headroom in the aft stateroom of your new 40-footer. Peter Nielsen

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