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67data points analyzed by Sailpages.com to compile this OYSTER 66 buyer’s report
OYSTER 66

OYSTER 66

Oyster MarineπŸ‡¬πŸ‡§Β· Design: Rob Humphreys
from 200512 built
$7.0K – $19K est. annual maintenance
Bluewater CruisermonoMasthead SloopFin

Specifications

Hull

LOA66.83 ft
LWL57.74 ft
Beam17.98 ft
Draft8.83 ft
Displacement87,633 lb
Hull speed1.34·√LWL10.2 kn

About the OYSTER 66

Sailpages Buyer's Take

The Oyster 66 is a substantial, heavy-displacement cruising yacht designed by Rob Humphreys and built by Oyster Marine, with a production run of 12 hulls completed in 2005. Its design emphasizes comfort and stability, evidenced by a high comfort ratio of 47.79 and a displacement of 87633.0 lb.

Best for:
This vessel is ideally suited for serious bluewater cruisers and families seeking a spacious, stable platform for long-range offshore passages, prioritizing comfort and safety over high-performance racing.
Bluewater capability:
With a low capsize ratio of 1.62 and a high D/L ratio of 203.23, the Oyster 66 exhibits excellent offshore stability and seaworthiness, making it highly capable for extended bluewater passages.
Comparables:
Comparable vessels include the Hallberg-Rassy 54 and the Swan 651, as they share similar heavy-displacement characteristics, robust construction, and a focus on offshore cruising capability from the mid-2000s era.

Performance

Comfort47.8
Capsize1.62
SA/Disp20.4
Disp/Len203

Pricing

We don't have market pricing data for the OYSTER 66 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 66.83ft LOA. Actual costs vary by condition, usage, and local rates.

$/ft/mo
Annual Maintenance
$7.0K – $19K
Hull, rigging, sails, engine service
Annual Docking
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Annual Insurance
N/A
No price data available

Known Issues & Pre-Purchase Inspection

2 reported issues across 2 systems for the OYSTER 66, compiled from owner reports in sailing forums and owner-association material.

1 critical1 major
Rigging1Rudder1

Unlock the full inspection report

Thinking of buying a OYSTER 66? 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 2 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

Similar Sailboats

Which engine powers your OYSTER 66?

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 OYSTER 66

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