O'Day sailboats for sale

Buying a used O'Day: matching a hull to its era, not just its model number

O'Day built boats for roughly three decades under two different conglomerate owners before an abrupt 1989 bankruptcy, and nearly all of its cruising range came out of one recurring design office. That combination means a used O'Day is usually a safer bet on construction consistency than on any single model's reputation — the more useful question for a buyer is which era and design lineage a given hull belongs to, since that tells you more about what to expect below the waterline than the model number alone.

Which era to target

Nearly all of O'Day's cruising models, including the 20 through the 26, came out of the same design office, C. Raymond Hunt Associates, in a run from 1972 to 1987 — a boat from that stretch of the lineup won't surprise you structurally as long as you already know what to check in the deck and hull-to-deck joint (see below). The clear exception is the 1985 O'Day 40, the company's largest and last flagship: its hull is cored where the rest of the range is solid, which calls for a different moisture-testing approach below the waterline than on any other model in the lineup. Diesel auxiliaries also show up earlier here than at many competitors, since O'Day was among the first major builders to standardize on them, so don't assume an inboard diesel on an older hull is necessarily a later repower. Design credit for the O'Day 40 itself is unsettled in the record — split between Hunt Associates and French designer Philippe Briand — so treat any seller's confident answer on that point with some skepticism.

What to inspect across the range

Chainplates are the single most consistently flagged concern across models and reviewers: Good Old Boat traced leaks on the O'Day 25 to missing tabbing between the deck and bulkhead, the Sailboat Guide review of the O'Day 28 pointed to both stanchion-adjacent leaks and worn forward chainplates, and Cruising World reported ongoing chainplate water intrusion on the O'Day 27 — the same failure point recurring across three different hull sizes and eras. Soft deck core tracks the same pattern, showing up near fittings and centerboard trunks on the 25 and 28 in particular. Keel condition is configuration-specific: SpinSheet's review of the fin-keel O'Day 40 describes a hairline crack at the front of the keel-to-hull joint nicknamed the "O'Day Smile," plus likely osmotic blistering below the waterline absent remedial repairs, while the same publication's review of the cast-iron-keeled 34 and 35 is blunter, finding that most examples reflect "a rather poor job of preparation and preserving the metal." Centerboard boats add one more recurring item worth budgeting for: routine inspection of the trunk and pivot hardware.

Navigating the lineup

The range runs from the Day Sailer and Rhodes 19 dinghies through 19-to-26-foot trailerable keel-centerboard cruisers to 28-to-40-foot coastal boats built mostly from the same Hunt Associates design lineage, so size and keel type separate the models more than any change in construction philosophy does. The full model directory on this page breaks the lineup out by hull so you can line up a size and keel configuration against how the boat will actually be sailed.