Tripp 33 Sailboat Review, Specs, and Listings

Design Brief & Intent

The core mission of the Tripp 33 was to dominate regional handicap fleets under the IMS and PHRF rating systems while remaining manageable for a dedicated amateur crew. In an era where competing designs were either heavy, compromised cruiser-racers or radical, unrated ultra-light displacement boats, the Tripp 33 carved out a unique niche. It was built to offer sportboat-like acceleration on downwind legs while maintaining the upwind punching power of a much larger, deep-keeled yacht.

To achieve this, the interior of the Tripp 33 was kept uncommonly Spartan. Structurally, Carroll Marine relied on molded fiberglass modules and structural bulkheads to provide stiffness, leaving the interior clean, bright, and highly utilitarian. The joinery is minimalist, featuring white laminate surfaces and exposed fiberglass skins that highlight the high quality of the build. While there are berths, a simple galley, and a marine head, the accommodation lacks the warm wood paneling, deep cushions, and storage capacity found in dedicated cruising yachts of the same length. The interior is engineered for the fast-paced environment of offshore racing—where off-watch crew need quick access to pipe berths, and sails must be packed, hauled, and stored below deck without damaging decorative woodwork.

Variations & Configurations

While some sisterships of the era were built with fixed fin keels, the defining feature of the Tripp 33 production run is its lifting keel configuration. This design utilizes a highly engineered vertical drop-keel with a high-aspect composite fin terminating in a concentrated lead bulb. With the keel fully extended to seven feet, the boat gains immense righting moment and efficiency when clawing to windward. When retracted to its shallow-draft limit of just under five feet, the boat can navigate shallow harbors, negotiate thin coastal waterways, and sit comfortably on a custom yard cradle or trailer.

The rig is a high-aspect fractional sloop layout with swept-back spreaders, featuring a massive mainsail and non-overlapping headsails that streamline tacking maneuvers and simplify short-handed sail handling. Auxiliary power was standardly provided by a small, lightweight 12-horsepower inboard engine—typically a two-cylinder Westerbeke diesel—designed to meet class rules and provide basic harbor maneuvering while keeping the boat’s overall displacement as low as possible.

Sailing Performance & Handling

The sailing characteristics of the Tripp 33 are defined by its exceptional power-to-weight ratios. With a displacement of just 6,100 pounds and a highly potent sail plan, the boat boasts an impressive sail area to displacement ratio of 25.88. In light air, this means the Tripp 33 breaks away from traditional cruiser-racers instantly, ghosting along at or near wind speed while heavier hulls remain stuck in the water.

Its displacement to waterline length ratio of 124.05 indicates a very light-displacement hull form that is easily driven and highly prone to planing or sustained surfing downwind. Under asymmetrical or symmetrical spinnakers in a breeze, the Tripp 33 is an absolute rocket, easily reaching double-digit speeds while remaining surprisingly controllable.

However, this performance comes with the trade-off of a lively ride. The comfort ratio of 14.25 underscores that this is a light, stiffly sprung sportboat. In a chop, the ride is highly active, and the crew will feel every wave crest. Helming the boat requires concentration; it responds instantly to the rudder and sail trim, behaving more like a high-performance dinghy than a traditional keelboat.

The capsize screening ratio of 2.26 indicates that the boat has a relatively wide beam relative to its light displacement, placing it outside the traditional boundary for passive, self-righting blue-water cruisers. Under sail, stability is heavily reliant on its 44.26% ballast-to-displacement ratio and the deep leverage of its bulb keel, keeping the boat remarkably flat and stiff in moderate air. But as the breeze builds upwind, early reefing and active mainsheet trimming are mandatory to prevent excessive heel and keep the boat sailing in its optimal "groove".

Known Issues & Triage

Because Carroll Marine built these hulls using lightweight cored fiberglass methods typical of high-performance yachts of the 1990s, age-related structural triage is common.

Core Saturation and Delamination: The hull and decks utilize a balsa core to achieve stiffness without adding weight. Over decades of hard racing, moisture can penetrate the laminate through improperly bedded deck hardware, stanchion bases, or traveler tracks. Buyers must perform a rigorous moisture-meter survey and percussion hammer test across the deck and topsides. Wet spots must be isolated, the hardware removed, and the core replaced with epoxy and new core material before being vacuum-bagged and re-sealed.
Keel Trunk and Lifting Mechanism Wear: The vertical lifting keel places high shear loads on the internal keel trunk and guide plates. Over time, the internal guide shims can wear down, leading to "clunking" or slop in the keel when sailing upwind or at anchor. The lifting winch, cable attachment points, and locking pins must be inspected for stress cracks and galvanic corrosion.
Mast Step and Chainplate Loads: The high rig tension required to keep the fractional headstay taut places immense load on the internal structural grid. The chainplate attachments and the area surrounding the keel-stepped mast require structural inspection to ensure there are no signs of fiberglass fracturing or compression settling.

Modernization & Upgrades

Most Tripp 33s still actively sailing have undergone significant updates to stay competitive and easy to handle in modern fleets.

Sprit Conversions: A highly popular upgrade among modern owners is the addition of a fixed or retractable carbon fiber bowsprit. This allows the removal of the heavy aluminum symmetrical spinnaker pole and allows the boat to fly modern, high-performance asymmetrical spinnakers, which drastically simplifies downwind sailing for short-handed crews.
Modernized Propulsion: The original two-cylinder Westerbeke diesels are often at the end of their reliable service lives. Many owners have chose to repower with modern, lightweight, freshwater-cooled diesel engines or have opted to convert the boat to electric propulsion. Given the boat’s weight sensitivity, an electric motor paired with a lightweight lithium (LiFePO4) battery bank is an increasingly viable way to shed weight while retaining basic harbor-maneuvering capabilities.
Running Rigging & Electronics: Replacing heavy wire-to-rope halyards with modern Dyneema lines and retrofitting the cockpit with wireless, high-speed wind and depth instruments are standard upgrades that enhance both performance and ease of use.

The Verdict

The Tripp 33 is not a boat for the casual weekend cruiser looking for a floating cottage. It is a finely tuned, highly responsive racing machine built for those who love the art of sailing fast. For the sailor who wants a boat that is exhilarating to steer, highly competitive in local handicap racing, and capable of being trailered or kept in a shallow slip, this rare design offers an unmatched level of performance per foot.