
CHESAPEAKE 20
Specifications
Hull
| LOA | 20 ft |
| LWL | 15.58 ft |
| Beam | 6.58 ft |
| Draft | 4.42 ft/ 0.58 ft min |
| Displacement | 950 lb |
| Ballast | 150 lb |
| Hull speed1.34Β·βLWL | 5.3 kn |
About the CHESAPEAKE 20
Sailed mainly on the West River of Chesapeake Bay (US). The first 40 boats were built by the designer from 1939-1943. A fiberglass version was first available in 1989. Current racing rules allow a trapeze but no spinnaker. See class web site for more details.
The Chesapeake 20 is a historic 20-foot fractional sloop designed by Ernest H. Hartge and built by Ernest H. Hartge (USA) between 1939, with a total production of 250 hulls. As a vintage vessel with a displacement of 950.0 lb, it represents a classic era of American small-boat design, requiring careful evaluation of its age-related structural integrity.
- Best for:
- This boat is best suited for coastal day-sailing and light cruising, appealing to owners who value classic aesthetics and manageable size over heavy offshore capability. Its light displacement and small footprint make it ideal for trailerable use and access to shallow waters.
- Bluewater capability:
- With a low displacement of 950.0 lb and a comfort ratio of 7.06, the Chesapeake 20 is not designed for bluewater cruising and is strictly limited to protected coastal waters due to its light ballast and vintage construction.
- Comparables:
- Comparable boats from this era include other 1930s-1940s trailerable sloops like the Pearson 16 or early O'Day models, which share similar fractional rig configurations and light displacement characteristics. These vessels are comparable due to their shared role as accessible, entry-level cruising platforms designed for local waters.
Performance
Images
Pricing
We don't have market pricing data for the CHESAPEAKE 20 yet. If you own one, help other buyers β what did you pay for it? Reports build a community price estimate over time.
Estimated Cost of Ownership
Based on 20ft LOA. Actual costs vary by condition, usage, and local rates.
Known Issues & Pre-Purchase Inspection
3 reported issues across 3 systems for the CHESAPEAKE 20, compiled from owner reports in sailing forums and owner-association material.
Unlock the full inspection report
Thinking of buying a CHESAPEAKE 20? 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.
- β All 3 specific issues β severity, symptoms & fixes
- β Model-specific pre-purchase inspection checklist
- β 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
Similar Sailboats
Which engine powers your CHESAPEAKE 20?
We haven't confirmed the engine for this model yet. If you own or know one, tell us β as owners report in, we build an accurate picture over time.
Already know your engine? Search all engines β to find its exact parts.
Used sails that fit the CHESAPEAKE 20
Checking eBay for sails sized to this boat's rigβ¦


