Is Bigger Always Better? 4 Reasons Why You Should Learn to Sail on a Small Boat

Over 40 years ago, I learned to sail on a windsurfer—about as small as you can get in the realm of sailboats. Since then, I’ve sailed on nearly every size and style of sailboat up to a 52’ catamaran. Smaller boats are a lot more fun. And by far, they are the best option for learning to sail. Here’s why:

Large Catamaran

Is bigger better when learning to sail?

More Responsive:

I took an American Sailing Association certification class taught on a 32’ Beneteau. Its unresponsiveness shocked me. On a Hobie, you immediately feel and see the effect of the wind—the boat heels, the sail fills or begins to flap, the sheet line becomes taught, even the rudder gives you feedback as to how the boat is sailing.

Larger Sailboat

Getting certified on a larger boat.

On larger boats, the skipper frequently glances up. That’s because the only way they can tell the wind direction in many cases is by looking at the wind vane on top of the mast. A big heavy boat doesn’t jump in a wind gust, it takes a lot for it to roll. They are designed to be smooth and stable, which is great for multi-day cruises but not great for learning.

On the 52’ Lagoon I helped sail to Bermuda, all the controls were electronic.

Atop the flybridge.

You could steer, navigate, and adjusted sails by simply pushing buttons. Instead of looking up at the wind vane, you just looked at your space-shuttle-like instrument panel to see wind speed, direction, boat speed, ETA, etc. Great if you don’t want to be bothered with sailing but, once again, not good for learning.

Instrument panel on flybridge of 52' Lagoon catamaran

Instrument panel on 52′ Lagoon on the flybridge.

Look- no hands!

Immediate Feedback:

I learned to windsurf on a lake in the foothills of South Carolina. The wind currents coming over those hills changed direction and speed constantly. Every time I misread a wind shift, I’d take a swim. My sailing improved tremendously in the winter when the water got cold and I didn’t want to get wet!

On a small boat (12 – 18 feet), you immediately know when you’ve done something right, and when you’ve done something wrong. Turn one way, and you pick up speed. Turn another, and you stop. That type of feedback is a great teacher. It also teaches you to read the wind which is usually the hardest thing for beginner students to grasp.

Flying a hull on hobie wave at Coastal Kayak in Fenwick Island, Delaware.

Sometimes small boats can be too responsive!

Less Confusion:

There must be some algebraic equation that calculates the number of lines (ropes) required for each additional inch of boat length. It gets a little out of control—uphaul, downhaul, boom vang, traveler, main sheet, jib sheet, etc, etc. The best boat for learning will have one sail and one line to control that sail. You learn faster and more thoroughly with fewer distractions.

Young sailor at Coastal Kayak

Coastal Kayak sailing student learning how fun and easy it is to sail.

More Accessible:

We have a few very simple questions sailors must answer prior to renting a boat from us. Surprisingly, folks who only have big boat sailing experience have problems answering those basic questions. On a small boat, you learn weight distribution and how to turn to avoid capsizing, or you get wet. Those aren’t really issues on a big boat.

Chances are you’ll find more opportunities to rent small boats than big boats. Regardless of the requirements of the rental business, the solid skills you learned on small boats will make for a much more enjoyable outing.

Hobie sailboat rentals at Coastal Kayak in Fenwick Island

Hobie rentals are available in many places including Coastal Kayak in Fenwick Island, Delaware.


I’ve been teaching sailing for over 20 years and use the 14’ Hobie Wave with a single sail for all of my beginner lessons because it is stable, responsive, and simple. Once the student learns to read the wind and master the basics, we talk about moving up to a larger boat. 

But the most fun I ever had was learning to windsurf. So don’t be in a rush to upsize. In my experience, when sailing, bigger is not better!

Sailing instructor Captain Mitch Mitchell at the helm of a Hobie Wave.


Mitch Mitchell


(AKA Capt’n Wally)

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