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179data points analyzed by Sailpages.com to compile this CSY 37 buyer’s report
CSY 37

CSY 37

Caribbean Sailing YachtsΒ· Design: Peter Schmitt
$37,514 avg$22,156 – $53,000 (4 listings)1978–198182 built
$2.3K – $6.2K est. annual maintenance
Bluewater CruisermonoCutterFin
CSY (Caribbean Sailing Yachts) history β†—

Specifications

Hull

LOA37.25 ft
LWL29.17 ft
Beam12 ft
Draft5.25 ft
Shoal Draft4.67 ft
Displacement22,000 lb
Ballast8,500.8 lb
Hull speed1.34·√LWL7.2 kn

Rig & Sails

Iforetriangle height46.5 ft
Jforetriangle base14.8 ft
Pmainsail luff40.6 ft
Emainsail foot13.1 ft
FLforestay14.8 ft
Mainsail631.3 sq ft
Jib (100%)344.1 sq ft
Spinnaker585 sq ft

About the CSY 37

Available with a shoal draft keel, 1 and 2 stateroom models. Most were first sold to Charter companies.

Sailpages Buyer's Take

Designed by Peter Schmitt and built by Caribbean Sailing Yachts from 1978–1981, the CSY 37 is a robust cutter-rigged cruising yacht with 82 hulls produced. Its heavy displacement of 22000.0 lb and high comfort ratio of 39.32 reflect a design prioritizing stability and seakeeping over pure speed.

Best for:
This boat is ideally suited for serious coastal and offshore cruisers who value a stable, comfortable motion and ample interior volume over high-performance sailing. It appeals to owners willing to perform diligent maintenance on its aging systems and deck structure.
Bluewater capability:
With a displacement of 22000.0 lb, a low capsize ratio of 1.72, and a proven fin keel design, the CSY 37 is well-regarded for bluewater cruising due to its exceptional stability and heavy construction.
Comparables:
Comparable vessels include the Cal 40 and O'Day 38, which share similar heavy-displacement characteristics and cutter rigs from the late 1970s. These boats offer similar interior layouts and offshore capability but often lack the CSY's specific Schmitt design nuances.

Performance

Comfort39.3
Capsize1.72
SA/Disp12.5
Disp/Len396
Bal/Disp38.6

Estimated Value

Low Confidence
Based on 4 listings
Low
$21,728
Estimated Value
$29,098
High
$36,519
Inflation-adjusted to 2026 USD

Estimated Cost of Ownership

Based on 37.25ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$2.3K – $6.2K
Hull, rigging, sails, engine service
Annual Docking
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Articles & Reviews

Known Issues & Pre-Purchase Inspection

20 reported issues across 9 systems for the CSY 37, compiled from owner reports in sailing forums and owner-association material.

5 critical7 major8 minor
Structural5Engine4Deck3Rudder2Hull2Rigging1Keel1Electrical1Plumbing1

Unlock the full inspection report

Thinking of buying a CSY 37? This is an in-depth report on the faults this model is known for β€” so you know exactly what to check when you walk the boat. For the price of a coffee.

  • βœ“ All 20 specific issues β€” severity, symptoms & fixes
  • βœ“ Model-specific pre-purchase inspection checklist
  • βœ“ Downloadable PDF to take to your surveyor β€” yours to keep

One-time $2.99 Β· secure checkout by Stripe Β· instant access Β· 30 days online, PDF yours to keep

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Engine Parts & Maintenance

The engines most commonly fitted to this model. β€œAll parts” opens the engine's full catalogue; each part links to a matching listing on Amazon or eBay matched to its part number.

Don't see your engine listed? Search all engines β†’ to find parts for the exact engine fitted to your boat.

Prices are reference figures β€” confirm the current price on Amazon. Always confirm fitment against your engine's model and serial before ordering. As an Amazon Associate we earn from qualifying purchases.

Used sails that fit the CSY 37

Checking eBay for sails sized to this boat's rig…