Windward 21 (Macgregor) Information, Review, Specs

History and Design

The Windward 21's genesis in the mid-1960s reflects Roger MacGregor's overarching design philosophy: to create affordable, easily manageable, and trailerable sailboats that would appeal to the broadest possible market. His vision prioritized accessibility and cost-effectiveness, often resulting in designs that made sailing attainable for many new owners. Windward Yachts, operating from Jacksonville, Florida, during a focused period, contributed to this vision by manufacturing small fiberglass sailboats, a common and durable material choice for recreational boats of that era.

The boat's design incorporates a swing keel, a crucial feature indicated by its variable draft, which ranges from a mere 1.0 foot when retracted to a substantial 5.5 feet when fully deployed. This allows the Windward 21 to navigate shallow coastal waters and be easily beached or trailered, greatly enhancing its versatility and appeal as a trailer-sailer. While the provided specifications list a "cutter" rig, which is a less common configuration for a boat of this size, it is important to note that many similar models, such as the Venture 21 and Macgregor 21, were typically equipped with a masthead sloop rig. This indicates a straightforward sail plan, prioritizing ease of handling.

Sailing Performance and Handling

Given its compact size, the Windward 21 was not designed for blistering speed or upwind prowess, but rather for enjoyable and accessible sailing. Owners of similar models frequently note that the boat performs admirably downwind and on a reach, offering a lively and fun experience. Its maximum hull speed is approximately 5.76 knots, providing respectable performance for a vessel of its length. The swing keel is a defining characteristic, offering excellent access to "skinny water" and enabling the boat to be easily launched and retrieved, making it ideal for exploring shallow coves and inland waterways. While generally easy to handle, some anecdotal reports for its cousins, the Venture 21 and Macgregor 21, have occasionally noted challenges with upwind performance and potential rudder issues.

Accommodations and Layout

The interior of the Windward 21, much like its closely related counterparts, provides basic, functional accommodations suitable for overnight stays or weekend cruising. Descriptions of similar models often highlight a "Spartan interior" with "low headroom," a common characteristic of trailerable sailboats in this size range. The typical layout includes a V-berth forward, a main cabin area that serves as a rudimentary salon, and space for a portable head (porta-potty). A small galley area, often equipped with minimal facilities, would have been common. Storage is generally limited, but owners frequently praise the potential for customization and modification to suit individual needs. Some models incorporated foam blocks for flotation within the interior, serving as an important safety feature.

Owner's Perspectives

Owners of the Windward 21 and its close relatives, the Venture 21 and Macgregor 21, often highlight the boat's strengths as an affordable and capable entry-level sailboat. Its trailerable nature is consistently praised, allowing for easy transport to various sailing destinations and expanding its utility beyond a single home port. The swing keel is a significant advantage for shallow water access, and the boats are generally considered excellent for those looking for a first sailboat or a simple weekender.

However, prospective owners should be aware of some frequently mentioned considerations. The build quality, while adequate for its price point and era, may not match that of more robust offshore cruisers. Common maintenance areas include inspecting and addressing potential issues with the swing keel pivot bolt, which is critical for the keel's proper function and safety. Rudder integrity and the condition of deck fittings are also noted as areas to watch, with older boats sometimes developing leaks or requiring re-bedding of hardware. Despite these potential points of attention, the Macgregor Windward 21, along with its siblings, has earned a reputation as a solid and enjoyable platform for casual sailing, offering significant value to those seeking an accessible and versatile small cruising sailboat.