Windward sailboats for sale

Buying a used Windward: identify the builder before anything else

A boat listed simply as "Windward" could be any of three unrelated products: a one-design racing scow from Wisconsin, a home-assembled kit cruiser from Minnesota, or a cruising boat from a third builder with almost no documented history. Figuring out which one you're looking at matters more than almost anything else you'll evaluate, because the three differ in construction, in how consistent quality is from one hull to the next, and in how much can even be verified about them. The model name on the transom — Boatworks Butterfly, Windward 21, or one of the 24, 30, 36, and 850 — settles the question immediately, and the rest of a buyer's approach follows from that answer.

Which era to target

For the Boatworks Butterfly, era matters less than usual: the class has been virtually unchanged since 1962, and the builder describes its more recent updates as improvements to build quality and durability rather than to performance, meaning an older hull isn't giving up speed to a newer one. What matters more is condition — the class was designed as a fun, lightweight, small-lake scow, and a well-kept older example competes on equal terms.

For the Windward 21, the defining question isn't era but origin. Luger Industries sold the design both as a home-build kit and as a factory-assembled boat. Before anything else, find out which kind a given 21 is — a home-built hull carries the fingerprints of its individual builder, while a factory-assembled one reflects Luger's own shop standard instead.

For the 24, 30, 36, and 850, there's no documented era to target at all. Our catalog attributes these to a third builder, separate from the other two, but published sources proved too scarce even to confirm that company's identity, let alone a construction history — so a buyer evaluating one of these four is working mostly from the boat's own papers and a survey, not from a documented production record.

What to inspect across the range

On the Butterfly, inspect the toe rails closely: a reviewer examining a 1977 example singled out that fitting — loose, badly repaired — as the recurring weak point on boats like it. On a kit-built Windward 21, inspection should lean harder on general build quality throughout the boat, since consistency was never guaranteed by a single factory process the way it would be on a boat built entirely in-house.

Navigating the lineup

Three unrelated builders means three different ownership experiences, not three trims of the same boat. The full model directory on this page separates the Butterfly, the 21, and the 24/30/36/850 lineup — confirm which one a listing actually is before comparing it to anything else.