CSY 44 Sailboats For Sale

The CSY 44 is a heavy-built, bluewater-oriented 44-foot production from Caribbean Sailing Yachts (CSY) produced in the late 1970s and early 1980s. Examples of the model include walk-thru or walkover layouts and both cutter and cutter-ketch rigs; listings identify the Walk-Thru Cutter Ketch and Walkover variants. CSY built these boats to Lloyd’s design and boatbuilding requirements, and the design has been cited in period coverage such as Cruising World’s list of notable sailboats.

Construction is a defining feature: hulls and decks are solid fiberglass with a heavy layup. One listing documents the hull at up to 1.5 inches of solid fiberglass with multiple layers, and the only wood used in production is laminated structural stringers, bulkheads, and interior joinery rather than wood lamination in the hull. At least some boats have an internally encapsulated keel with removable concrete ballast so draft can be reduced when desired.

Accommodations on representative CSY 44s emphasize volume, storage and robust joinery. Multiple listings describe two-cabin arrangements with a separate aft cabin accessed through the cockpit, a forward v-berth, and two heads—one aft en suite and a second opposite the galley. Headroom reported in listings is about 6.7 ft in the salon on at least one example. The salon is described as bright and spacious with settees that can convert to berths, and galleys are arranged for extended cruising with cooking and refrigeration facilities.

Deck and cockpit arrangements favor offshore use: center cockpit layouts provide seating and dedicated storage, and rigging configurations cited include cutter rigs with self-tacking staysails and ketch options. Maintenance history on individual boats varies; recent examples have documented work such as engine rebuilds, thru-hull and system renewals, deck nonskid repainting, blister repairs with epoxy barrier coats, and electrical system reviews. Taken together, the construction, layout and documented maintenance of CSY 44s align with the model’s reputation in listings as a sturdy, passage-capable cruiser.