MacGregor Windward 21 Sailboats for Sale & Market Overview

Hull type

Monohull · wing

Rig

Cutter

LOA

21' · 6.4 m

Displ.

1,200 lbs · 544 kg

First year

1966

The Windward 21 is a quintessential example of the early trailersailer movement that revolutionized American weekend sailing in the 1970s and 80s. Designed by the prolific Roger MacGregor and produced by Windward Yachts in Jacksonville, Florida, this 21foot sloop was engineered to bridge the gap between a highperformance dinghy and a heavy keelboat. By utilizing a retractable swing keel, the Windward 21 allowed sailors to explore shallow coastal waters and inland lakes that were previously inaccessible to traditional cruisers. Though the Jacksonvillebased builder operated for a relatively short window, their production of this MacGregor design remains a notable entry in the history of Florida boatbuilding, offering a lightweight, fiberglass hull that prioritized ease of transport and affordability.