Design and Construction
The Oyster 66 is strong, with a solid laminate hull and a beefed-up balsa-core deck anchor. Oyster used two English yards to fit out the 66s, and their grasp of production quality control is impressive. The joinery detail, specially commissioned for Oyster by Dick Young Designs to celebrate the new millennium, features shadow-gap joints, custom Oyster 2000 logos on locker knobs, and checkerboard floor panels. A variety of wood finishes are offered, cherry and American oak among them. For compliance with MCA regulations, watertight doors may be fitted forward and aft.
Rig and Handling
Under sail, the 66 rewards push-button simplicity without sacrificing control. The Hood rollaway mainsail is hydraulically driven and the outhaul electrically controlled, while the high-clew yankee is set from the cockpit using Reckmann hydraulic furling gear anchor. Huge Lewmar electric winches allow exact trim, and the large center cockpit with twin wheel positions and quarter seats aft gives several vantage points from which to enjoy the sailing. A powerful bow thruster helps angle the yacht in rough seas, and she maneuvered well even when conditions were difficult.
Her behavior at sea rests on a fairly heavy displacement of 83,774 pounds coupled with a modern underwater shape, keel, and rudder. The underbody is deeper than those of lightweight flyers but shallower than traditional cruisers, and does not have flat surfaces to pound. The keel has twice the chord length and maybe half the span of a high-performance racer/cruiser, but the shape is effective, and a ballast bulb at the tip lowers the center of gravity for good stability while reducing drag. The skeg-hung rudder is large enough to take big bites of water for quick, accurate steering response.
Accommodations
The saloon area is set at a height to give a line of sight outboard through the Deck Saloon windows, allowing a panoramic vista, and the spacious saloon includes an elevated seating and table area that will accommodate about 10 people. Down a few steps, the lower saloon holds the galley and a pair of armchairs suited to reading or quiet conversation; the galley is open to the saloon and feels very spacious, placed at an unobtrusive lower level with plentiful counter space and stowage. The navigation station on the saloon's starboard side has a large chart table with space above for a navigation and communications suite.
Private quarters are generous. The master suite aft has a queen-size berth, a settee, two large hanging lockers, and a lot of drawer space. Port and starboard double cabins forward of the master share a single head to port, while forward of the saloon are two double cabins, both with en suite heads. All heads have VacuFlush toilets, full standing headroom, ample locker space, and Avonite faux granite around the sinks. The forepeak contains a cavernous sail locker and the usual anchor locker, with forward stowage for light-weather sails, a spare anchor, and a deflated second dinghy. A lazarette right aft held fenders, spare parts, a dive compressor, and other gear on the reviewed boat.
Ownership and Outfitting
The 66 offers an attractive combination of features normally associated with much bigger yachts, and the builder describes a really well thought out package of accommodation, good looks, and performance. The hard-bottom inflatable is launched via electric davits one person can operate. With proven handling and performance under sail and power, the yacht was designed and built for offshore cruising in comfort and safety, run by the owners or crew.
The Verdict
The Oyster 66 is a serious offshore cruiser that wraps superyacht-scale living into a manageable 66-foot hull. Her weight, modern underbody, and bulb-keel stability make her a steady sea boat, while hydraulic rigging and electric winches reduce crew workload. The deck-saloon layout and custom millennial joinery give her a distinctive, roomy interior rare in this size bracket.
Pros
- Solid laminate hull with beefed-up balsa-core deck and MCA-optional watertight doors
- Hydraulic mainsail and yankee furling with electric winches for short-handed control
- Panoramic deck-saloon vista and elevated saloon seating for ten
- Five cabins with en suite or shared heads and a large aft master suite
- Skeg-hung rudder and bulb-tip keel for stable, accurate steering
Cons
- Only 13 built, limiting brokerage availability
- Heavy displacement trades outright acceleration for offshore steadiness
- Open galley to saloon may not suit all privacy preferences





