Windward 21 Macgregor

Designed by Roger Macgregor in the mid-1960s, this compact cutter represents an interesting chapter in small boat design from the era when trailerable sailboats were gaining popularity. Built by Windward Yacht from 1966 to 1969, the design showcases several practical features that made it appealing to sailors seeking an affordable entry into cruising. The swing keel configuration allows for shallow water exploration and easy trailering, while the cutter rig provides excellent sail handling options and weather helm control. At 1,200 pounds displacement with 400 pounds of ballast, this fiberglass boat strikes a reasonable balance between portability and stability for its size class. With a comfort ratio of 7.45, the boat leans toward the sportier side of the spectrum, making it well-suited for day sailing and weekend coastal cruising rather than extended offshore passages. The 175 square feet of sail area provides adequate power for typical conditions, while the hull speed of 5.76 knots offers respectable performance for a boat of this length. The design works best for sailors interested in coastal exploration, club racing, or learning cruising fundamentals in protected waters. Its compact size and swing keel make it particularly appealing for those with limited marina access or storage constraints.

No owner reviews yet — be the first to share your experience with this boat.