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67data points analyzed by Sailpages.com to compile this CHESAPEAKE 20 buyer’s report
CHESAPEAKE 20

CHESAPEAKE 20

Ernest H. HartgeπŸ‡ΊπŸ‡ΈΒ· Design: Ernest H. Hartge
from 1939250 built
$600 – $1.6K est. annual maintenance
Performance RacermonoFractional SloopVariable
Chesapeake 20 Class Assoc. β†—

Specifications

Hull

LOA20 ft
LWL15.58 ft
Beam6.58 ft
Draft4.42 ft/ 0.58 ft min
Displacement950 lb
Ballast150 lb
Hull speed1.34·√LWL5.3 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.

Sailpages Buyer's Take

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

Comfort7.1
Capsize2.68
SA/Disp41.5
Disp/Len112
Bal/Disp15.8

Images

boat photo
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2025 Annual Meeting, New Mailing List and More
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2023 Racing Schedule
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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.

$/ft/mo
Annual Maintenance
$600 – $1.6K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
N/A
No price data available

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.

2 critical1 minor
Rudder1Keel1Structural1

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.

  • βœ“ All 3 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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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 rig…