Daysailer sailboats for sale

Buying a used Daysailer: confirm which boat you're actually looking at

A listing under this make isn't necessarily a Day Sailer. Our catalog uses "Daysailer" as a make bucket for small day-sailing boats generally, and only one of the designs gathered under it is the genuine class Uffa Fox and George O'Day created in 1956: the O'Day Day Sailer, spelled as two words by the class and its owners' association. Also filed here, purely because they fit the same generic type description, are a Sea Sprite 23, a Cape Dory Typhoon, a Seafarer 23 Kestrel, and a "16" built by the unrelated Johnson Boat Works — each a distinct design with its own page and history, none of it applicable to a Day Sailer purchase. If you're shopping specifically for the O'Day/Uffa Fox boat, the rest of this guide is for you; if you landed here for one of the other four, look up that boat by its own name instead.

Which era to target

A genuine Day Sailer's features narrow down which model, and which era, you're looking at. Wood — thwarts, seats, cockpit sole — plus a centerboard lever, an open cuddy, and a transom deck are the telltales of the earliest I's, before foam flotation and self-bailing arrived. Built-in foam flotation, a smaller cuddy opening that doubles as a thwart, and a thinner transom built to take an outboard up to 7 horsepower without a bracket mark a Day Sailer II, introduced in 1971. For a buyer who races one-design, the model year on a Day Sailer III (O'Day built it between 1985 and 1990) is a dealbreaker rather than a detail: the class rules exclude it, over a transom freeboard raised past what Fox's original hull specified, so racing buyers should confirm eligibility before treating any III as a I or II equivalent. The boat offered new — a modified Day Sailer I with two sealed air tanks, a smaller-hatch cuddy flotation tank, and a forward bulkhead that lets it be righted and re-sailed after a capsize — is built in both a standard version with a deck-hinged mast and a racing version with a tapered, keel-stepped mast and internal halyards, so a buyer choosing new construction over a used O'Day-era hull should specify which one they want.

Navigating the lineup

Within this catalog's own listings, the II is the only row that represents the real class; a buyer set on a I or a III should expect to search beyond this specific model entry. It's also worth knowing, when weighing a decades-old O'Day-built hull against new construction, that the yard building new boats — Cape Cod Shipbuilding, under exclusive license — doesn't own the molds it builds from; the Day Sailer Class Association does, and licenses their use. The full model directory on this page separates the genuine Day Sailer from the other boats sharing this make, and is the place to confirm which listing you're actually evaluating.