Design and Construction
The original 44 paired a fiberglass hull and molded cockpit with cold-molded marine plywood decks and cabin top, while the cabin sides were solid mahogany, all either cold-molded or sealed with epoxy resin anchor. That wood-on-glass hybrid kept the topside structure traditional without going fully wooden, and the builder was confident enough to offer a lifetime hull warranty on the design anchor. In 2007, Cherubini’s nephew introduced the Mark II as a 30th-anniversary update; it brought a fully molded fiberglass deck and deckhouse with a foam core and vinylester resin, plus a slightly higher cabin trunk, slightly higher bulwarks, and system improvements over the original anchor. The Mark II therefore modernized the structure without altering the underlying hull shape that defined the class.
Hull Form and Performance
Designed with serious cruisers in mind, the 44 carries a 40-foot waterline inside an on-deck length of 44 feet 2 inches, and a narrow beam of 11 feet 6 inches kept the boat long and slim for fast passages anchor. An in-keel lead ballast of 12,000 pounds provided stiffness and stability when the winds increased, and the shoal keel with centerboard gave a minimum draft of 4 feet 10 inches and a maximum of 8 feet 10 inches for flexible gunkholing and tracking anchor. With a displacement length ratio of 195 and a sail area displacement ratio of 19.7, the boat is a heavy-displacement cruiser that still carries enough canvas to move; her theoretical hull speed is 8.47 knots anchor. Owners proudly recount her one-time win over the famous Running Tide in a Ft. Lauderdale-to-Key West SORC race, and a more recent first place finish in the 2007 Marion-Bermuda race anchor.
Rig and Deck Layout
The Cherubini 44 is ketch-rigged with the mizzen mast stepped in the forward cockpit, and the double headsail ketch rig allows for numerous possible sail combinations to balance the boat in nearly any condition anchor. The helm was separated from the main cockpit, and in practice the layout gives an elliptical steering cockpit aft and a rectangular crew cockpit forward, with the mizzen dividing the two anchor. Broad side decks with substantial bulwarks provide secure footing, and the long, low trunk cabin was well-lit and ventilated with watertight bronze portlights anchor.
Accommodations
From the cockpit you enter an aft cabin and navigation area, move forward to a starboard head with shower and a U-shaped galley to port, then a main saloon with port and starboard settees around a centerline drop-leaf table, and a forward cabin with hanging lockers and drawers on each side and a V-berth in the bow anchor. Most 44s were built on a semi-custom basis allowing original-owner input, so each interior varies slightly while following the same general arrangement, and the boat included custom built-down lockers and cabins anchor. The separation of helm and crew cockpit keeps sail handling away from the wheel, a layout that suits a cruising couple or short-handed crew who value distinct work and steering zones.
Power and Known Issues
Over the years these boats have been powered by a variety of manufacturers’ diesel engines ranging from 37 to the present 75 horsepower Yanmar, but early models with less than 50 horsepower were underpowered anchor. After the navigation station is removed, engine access is good, and if necessary the engine can quite easily be removed through the companionway hatch anchor. The relatively low freeboard can result in a wet ride if pushed hard in rough conditions, a trade-off of the low-profile deckhouse and slim hull anchor.
The Verdict
The Cherubini 44 is a small-series Herreshoff-inspired ketch that rewards the buyer who wants classic profile and shoal-draft flexibility without a wooden hull’s upkeep. The Mark II resolved the original’s plywood-deck maintenance question with molded composite structure, while the narrow beam and 40-foot waterline make for a quick, seakindly cruiser in the right hands.
Pros
- Rare design by John Cherubini with direct Herreshoff Ticonderoga lineage
- Shoal keel/centerboard with 4'10" to 8'10" draft range
- Ketch rig with mizzen in forward cockpit for many sail plans
- Lifetime hull warranty offered by the builder
- Good engine access once nav station removed; engine lifts out companionway
Cons
- Early sub-50 hp engines underpowered
- Low freeboard means wet ride when pushed hard
- Only 35 built; finding one and spares context takes patience








