Who designed the CSY 44?

Sources disagree. Cruising World credits 'Frank Hamlin, Peter Schmitt'; CSY's own company history, sourced from Van Ost and Schmitt directly, says the company worked initially with Ted Irwin and traces the 44's hull shape and raised aft deck to a resemblance with Irwin's center-cockpit designs; Soundings credits Van Ost's team working with Schmitt in 1976. Schmitt is the one name that recurs across every account.

What made CSY's construction different from other charter-era builders?

CSY's boats were built to unusually high standards of strength and durability because they went straight into hard bareboat charter use. The company's own CSY Guide claimed the boats met Lloyd's of London's design and construction requirements, and Practical Sailor, reviewing the CSY 37, called CSY boats 'probably the strongest production boats ever marketed.'

What's the difference between the CSY 44 walk-over and walk-through?

The walk-over, with a spacious cockpit and separate, unconnected staterooms fore and aft, was by far the more common configuration. The walk-through arrived only much later in the model's run, and only about 40 were built before CSY closed.

What happened to CSY?

CSY's manufacturing operation closed in 1981; the charter company continued another decade before closing and handing its bookings to The Moorings. Antigua Yachts, under owner John Coats, later acquired the CSY 44 molds and built roughly 20 to 30 examples as the Antigua 44.

How many CSY sailboats were built?

Soundings reports CSY grew into roughly the sixth-largest sailboat builder in the country, producing on the order of 400 boats between 1977 and 1981, across a line that started with the 33, 37, and 44 and later grew to include the 42 PH, 50, 51, and 505.

CSY Sailboats | Listings Port

Explore CSY sailboats and the details behind each model. If you are shopping for a CSY sailboat, we keep an eye out for Used CSY Sailboats.

Model ↕	Listings ↓	Year Built ↕	LOA (ft) ↕	Beam (ft) ↕	Draft (ft) ↕	Disp. (lbs) ↕	Hull ↕	Designer ↕	Rig ↕	Keel ↕
CSY 44	22 for sale	1977	44 ft	13.33 ft	6.5 ft	38,000 lbs	Monohull	Frank Hamlin/Peter Schmitt	Cutter	Fin
CSY 37	10 for sale	1978	37.25 ft	12 ft	5.25 ft	22,000 lbs	Monohull	Peter Schmitt	Cutter	Fin
CSY 33	1 for sale	1978	33.04 ft	11 ft	5 ft	15,300 lbs	Monohull	Peter Schmitt	Cutter	Fin
CSY 505	1 for sale	1987	50.5 ft	15.25 ft	5.75 ft	31,500 lbs	Monohull	Charles Morgan	Masthead Sloop	Long
CSY 42 PH	—	1986	42.33 ft	13.42 ft	5.42 ft	22,400 lbs	Monohull	—	Masthead Sloop	Fin
CSY 50	—	1986	50.08 ft	14 ft	5.92 ft	34,500 lbs	Monohull	Lazzara	Masthead Sloop	Fin
CSY 51	—	1985	51 ft	15 ft	5.5 ft	35,000 lbs	Monohull	Johan Valentijen	Masthead Sloop	Wing

CSY sailboats: the Caribbean charter operator that built its own heavy cruisers in Tampa

Caribbean Sailing Yachts began as a charter company, not a boatbuilder. Long before CSY put its name on a hull, John "Jack" Van Ost was running Caribbean bareboat bases and learning, fleet season by fleet season, what a boat built for paying strangers actually needed to survive.

Origins and ownership

Jack Van Ost, a New Jersey dentist and father of eight who had served as an Army captain in World War II and earned his DDS from the University of Minnesota in 1944, became a pioneer of Caribbean yacht chartering. He opened one of the first charter bases in the region, starting out of Red Hook, USVI, then moving to Tortola, BVI a year later, and launched CSY's first winter charter season in 1967 with sixteen Chris-Craft Capri 30s. By 1969 Van Ost had concluded his fleet needed a boat purpose-designed for cruising rather than off-the-shelf production stock, and working with designer Alan Gurney he developed the Carib 41, pairing a huge center cockpit with fore-and-aft staterooms.

Unable to find an outside builder who could deliver the quality he wanted at his price, Van Ost decided to build CSY's next boat, the 44, himself in Tampa. CSY sold its boats directly from the factory, without dealers or middlemen, and many, especially the 44 walk-over, went out under an agreement that put them into the CSY charter fleet for a set term before the boat reverted to its original buyer. At its 1981 peak, CSY was chartering 186 sailboats out of bases in the Florida Keys, Roatan in Honduras, the Bahamas, Tortola, and St. Vincent in the Grenadines. The manufacturing side closed that same year, undone by high interest rates and the deposits Van Ost had refunded on 44 orders when he chose to build the boat himself rather than farm it out; the charter company lasted another decade before closing and handing its remaining bookings to The Moorings. After CSY's closure, Antigua Yachts, under owner John Coats, acquired the molds for the 44 and resumed building a customized version under the name Antigua 44, producing roughly 20 to 30 of them through the 1980s.

The designers

CSY's design lineage runs through several names, and the record is not entirely tidy. The company's own account, sourced directly from Van Ost and Schmitt, says CSY "went into the boat manufacturing business, working initially with Ted Irwin," a well-known Tampa-area designer, and traces the 44's hull shape and raised aft deck to a resemblance with Irwin's center-cockpit designs of the era. Soundings instead credits Van Ost and his team with designing the 44 alongside Schmitt in 1976. Elsewhere, Cruising World's own listing credits the 44 to "Frank Hamlin, Peter Schmitt." Schmitt is the constant across every account: CSY's own site calls him "the designer of the CSY sailboats" through the late 1970s and early 1980s, and he is separately credited, in the late 1970s, with the CSY 33. Later in the company's life, naval architect Charles Morgan designed the larger CSY 505.

Construction through the eras

Charter duty set CSY's engineering bar: a bareboat had to hold up to a full season of charter guests, not just one owner's care. The company's own marketing book, the CSY Guide, told buyers its boats met Lloyd's of London's design and construction requirements. Soundings reports that CSY grew quickly into roughly the sixth-largest sailboat builder in the country, turning out on the order of 400 boats between 1977 and 1981.

Lines and generations

The core line comprised the 33, the 37, and the 44, initially offered in two configurations: the walk-over and the pilothouse. Most of the 44s built were walk-overs, with a spacious cockpit and separate, unconnected staterooms fore and aft; a walk-through 44 arrived only much later, and just about 40 were built before CSY went out of business. The lineup eventually widened further, adding the 42 PH, the 50, the 51, and, designed by Charles Morgan, the 505.

Who CSY is for

CSY built boats to a fleet-duty standard first, not to flatter a boat show floor, and that charter-first mandate still defines the brand. Buyers drawn to a boat engineered for durability first, backed by a factory willing to sell direct and put its own name behind years of charter use, are CSY's natural audience, more so than buyers chasing polish or a marquee designer name.