Used Windward 21 (Macgregor) Sailboats for Sale

Make
Macgregor
Model
Windward 21
Number Built
Production Year(s)
1966 - 1969

The Macgregor Windward 21 emerges as a concise and accessible sailboat, designed to introduce enthusiasts to the joys of sailing without the complexities and costs associated with larger vessels. Conceived by the prolific American naval architect Roger MacGregor and built by Windward Yachts of Jacksonville, Florida, this 21-foot monohull, produced from 1966 to 1969, shares significant design DNA with its close relatives, the Venture 21 and later Macgregor 21 models. It was crafted as a versatile trailer-sailer, aiming to offer a blend of sailing performance, shallow-water capability, and basic overnight accommodations for weekend cruising and daysailing.

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