The CSY 44 Sailboat
Specs & Key Performance Indicators

The CSY 44 was built by Caribbean Sailing Yachts (CSY), a company founded by David Walters in Florida in 1971. CSY specialized in building heavy-duty sailboats for chartering in the Caribbean, but also sold some boats directly to private owners or as kits for self-finishing. CSY went out of business in 1981 due to financial difficulties and lawsuits from unhappy customers.

A CSY 44 sailboat at anchor. 'CSY' stands for 'Caribbean Sailing Yacht'.A CSY 44 (Mid-Cockpit version)

Published Specification for the CSY 44 (Mid-Cockpit)

Underwater Profile: Fin keel & skeg-hung rudder

Hull Material: GRP (Fiberglass)

Length Overall: 44'0" (13.4m)

Waterline Length: 36'0" (11.0m)

Beam: 13'4" (4.1m)

Draft: 6'6" (2.0m), Shoal Draft version 5'0" (1.5m)

Rig Type: Cutter

Displacement: 38,000lb (17,327kg)

Designer: Peter Schmitt & Frank Hamlin

Builder: CSY Yacht Corp. (Caribbean Sailing Yachts)

Year First Built: 1977

The CSY 44 is a sailboat that has stood the test of time, capturing the hearts of sailing enthusiasts worldwide. Known for its remarkable design and sturdy construction, the CSY 44 embodies adventure, freedom, and challenge – sentiments that resonate with every sailor.

Design Ratios: The Key Performance Indicators

One of the key aspects that determine the performance of a sailboat is its published design ratios.

  • The Sail Area/Displacement Ratio (SA/D) of the CSY 44 is 16.65, suggesting that it offers a moderate performance under sail; it is neither too sluggish nor excessively high-strung.
  • Its Ballast/Displacement Ratio (B/D) is 38.3%, which indicates a good stability, especially under harsh weather conditions. This ratio is an important factor, as it reflects the boat's ability to right itself after being heeled over by the wind.
  • The Displacement/Length Ratio (D/L) of the CSY 44 is 301.4. This relatively high value means that the boat has a heavy displacement, which generally means a smoother, more comfortable ride, especially in rough waters.
  • The Comfort Ratio of the CSY 44 is 34.3, signifying that it provides a high level of seaworthiness and comfort for long-distance cruising. This makes it an excellent choice for those who value comfort and stability over pure speed.
  • The Capsize Screening Formula for the CSY 44 is 1.78, well below the 2.0 threshold, suggesting a lower risk of capsizing. This is a critical safety aspect for any potential buyer.

But what are these Design Ratios and how are they derived?

Alternatives & Options

The CSY 44 comes in various design and construction options. The most popular configurations are the sloop, cutter, and ketch. Each of these setups has its own advantages and are chosen based on the specific sailing requirements of the owner.

  • The sloop version of the CSY 44, with a single mast and generally two sails, is known for its simplicity and efficiency, making it a good choice for solo or short-handed sailing.
  • The cutter configuration, characterized by its split rig allowing for a more balanced sail plan, is ideal for offshore cruising. It provides greater flexibility and handling in varying wind conditions.
  • The ketch version, with two masts, allows for a variety of sail combinations making it extremely versatile, especially in high winds and over long passages.

There were also three hull versions of the CSY 44: Pilot House, Mid-Cockpit, and Walk Through.

  • The Pilot House version has an aft cockpit and a second steering station inside the cabin.
  • The Mid-Cockpit version, also known as the Walk-Over, has a centre cockpit and a separate aft cabin accessible from the deck.
  • The Walk Through version has a centre cockpit and an aft cabin connected to the main cabin by a passageway.

Most boats were delivered with the ketch rig, but some had a sloop or cutter rig.

The CSY 44 has two keel options: shoal or deep.

  • The shoal keel has a draft of four feet and a ballast of 10,000 pounds. The deep keel has a draft of six feet and a ballast of 12,000 pounds.
  • The shoal keel is more suitable for shallow waters, while the deep keel offers better stability and performance.

Praise or Otherwise

The CSY 44 received positive reviews from the sailing press for its sturdy construction, spacious interior, and good sailing performance.

Cruising World Magazine included the CSY 44 in its list of the 40 best sailboats of all time.

Sailboat Guide described the CSY 44 as "a ruggedly built mid-cockpit cutter also available in a pilothouse version" that was "as appealing to cruising traditionalists as it was to the charter fleet".

The boat has been praised for its strong, heavy-duty construction, spacious interior design, and impressive sea-keeping abilities.

Owners of the CSY 44 generally praise their boats for their durability, comfort, and seaworthiness. They also appreciate the ample storage space, tankage, and headroom that the CSY 44 offers.

Some common complaints from owners are the high maintenance costs, the lack of ventilation in some cabins, and the difficulty of finding spare parts.

Known strengths of the CSY 44 include its robust build, ease of handling, comfortable accommodation, and excellent performance in heavy weather.

However, like any boat, it is not without its weaknesses. Some reviews have mentioned the need for regular maintenance, particularly of the teak woodwork. Its heavy displacement also means it may not be as nimble or quick as lighter yachts in light wind conditions.

The Secondhand Market

The availability of CSY 44 sailboats on the secondhand market varies. As a classic and sought-after model, it often sells quickly when it does appear on the market.

Prices for a secondhand CSY 44 can vary widely depending on its age, condition, and the extent of its fittings and equipment. As a rough guide, prices tend to range from $80,000 to $150,000.

According to, as of September 2023, there are eight CSY 44s for sale ranging from $37,500 to $150,000.

As a buyer, undertaking the due diligence to understand the CSY 44 in depth is crucial. A boat is a significant investment, and choosing the right one could mean the difference between a joyous sailing experience and a financial disaster.

Similar Sailboats

When comparing the CSY 44 with other similar boats in its class, it holds its own in terms of performance, comfort, and seaworthiness.

It is often compared to the Tayana 42, another popular choice among cruising enthusiasts. While the Tayana might have a slightly more modern design, the CSY 44 typically offers more space and sturdiness.

The Endeavor 43 is another boat that is often compared with the CSY 44. Both boats are similar in size and displacement, but the CSY 44 boasts better offshore capabilities and a more comfortable ride, according to many sailors.

The CSY 44 is also often compared to the Gulfstar 44. While the Gulfstar may offer a faster speed, the CSY 44 provides a smoother, more comfortable ride, making it a preferred choice for long cruises.

While the CSY 44 may not be the newest or flashiest boat on the market, it has a proven track record and a loyal following among cruising enthusiasts. Its reputation for sturdiness, sea-kindliness, and comfortable living quarters make it a compelling choice for those planning long voyages.

The CSY 44 is more than just a sailboat; it's a lifestyle choice. For those who dream of exploring distant shores and embracing the challenges that come with it, the CSY 44 is the perfect vessel to turn those dreams into reality.

In conclusion, whether you're a seasoned sailor looking for a reliable cruiser or a newbie with dreams of circumnavigation, the CSY 44 offers a compelling blend of performance, comfort, and seaworthiness.

So, when you see a CSY 44 for sale, consider it not just as a purchase, but as an investment towards your future sailing adventures.

I wrote this article using GPT-4, OpenAI’s large-scale language-generation model, as a research assistant to develop source material. I wrote the final draft in its entirety and believe it to be accurate to the best of my knowledge.

Dick McClary, creator and owner of

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