Sailing Performance & Handling
The Windward 36 is characterized by its "stiff" sailing profile, a necessity for the gusty conditions of the Salish Sea. John Simpson’s designs are noted for their balanced helms and ability to track well even when pressed. With a moderately high displacement-to-length ratio typical of its era, the boat does not "skitter" over the water like modern light-displacement cruisers; instead, it punches through chop with a predictable, sea-kindly motion.
The sail plan is usually a masthead sloop rig, providing ample power in light airs—a common requirement for summer sailing in the Pacific Northwest—while remaining manageable when reefed down. According to historical design notes from John Simpson Ltd., the 36 was engineered with a lead keel that provides a low center of gravity, resulting in a high righting moment. Owners often report that the boat feels most at home on a close reach, where its deep-chested hull can leverage its momentum to maintain speed through lumpy seas. While not as nimble as a pure racing machine, its pointing ability is respectable for a cruiser of its vintage.
Interior Comfort & Variations
Inside, the Windward 36 reflects the craftsmanship of British Columbia’s "golden age" of boat building. The interior is typically finished in high-quality teak or mahogany, providing a warm, traditional atmosphere that contrasts with the "linered" fiberglass interiors of modern mass-produced yachts. The layout generally follows a classic offshore arrangement: a forward V-berth, a head with a shower to port, and a main salon featuring a U-shaped dinette that can often be converted into an additional double berth.
A notable feature of the Windward 36 is its generous galley, often positioned near the companionway for optimal ventilation and ease of use while underway. Because these boats were often semi-customized or finished by experienced owners from a factory-supplied hull and deck, interior variations are common. Some models feature a dedicated navigation station opposite the galley, while others prioritize a larger aft quarter-berth. Headroom is excellent throughout the main cabin, usually exceeding six feet, which makes the 36 a viable candidate for a live-aboard vessel or extended coastal cruising.
Known Issues & Buyer’s Checklist
Prospective buyers of a Windward 36 should focus on the specific aging characteristics of 1970s fiberglass construction. While the hulls are generally overbuilt and solid, the deck construction often utilizes a balsa or plywood core which is susceptible to moisture ingress.
- Deck Delamination: Pay close attention to soft spots around the stanchion bases, chainplates, and the mast step. Leaking hardware over decades can compromise the core material, requiring expensive "skin-and-replace" repairs.
- Chainplates: Given the age of these vessels, the stainless steel chainplates should be inspected for crevice corrosion, particularly where they pass through the deck.
- Propulsion: Many original models were fitted with Volvo Penta or early Yanmar diesel engines. Buyers should verify the availability of parts for these legacy powerplants or budget for a repower if the engine shows signs of excessive blow-by or cooling system scale.
- Osmotic Blistering: Like many boats from the early era of fiberglass, some Windward hulls have shown a tendency toward osmotic blistering. While usually cosmetic, a haul-out inspection is mandatory to determine the extent of any hull hydration.
- Rigging Age: Unless recently replaced, the standing rigging likely exceeds its safe operational lifespan. The swage fittings should be checked with a magnifying glass for hairline fractures.
The Verdict
The Windward 36 is a "sailor’s boat" that offers a level of structural integrity and aesthetic warmth rarely found in contemporary entry-level cruisers. It is a vessel designed for those who value durability and classic lines over the "condo-on-the-water" volume of modern designs. While it requires a buyer willing to manage the maintenance of an older hull, the rewards are a capable, prestigious, and handsome yacht that remains a staple of the Pacific Northwest cruising community.
Pros
- Exceptional seaworthiness and stability in heavy weather.
- High-quality interior joinery using traditional materials.
- Balanced handling characteristics thanks to John Simpson's naval architecture.
- Strong value-to-size ratio on the used market.
Cons
- Aging deck cores and systems require diligent maintenance and inspection.
- The IOR-influenced design may exhibit some "rolling" tendencies when sailing deep downwind.
- Limited production numbers make finding specific spare parts or sistership advice more difficult than for mass-market brands.








