1966 Chevrolet Chevelle SS

Price: $84,997

The 1966 Chevrolet Chevelle SS 396 is widely considered the high point of the first-generation Chevelle's design cycle. Chevrolet had introduced the Chevelle in 1964 as a mid-size answer to the Ford Fairlane, but it was the 1966 model year that brought the sharpest styling the platform ever wore — a longer hood, a cleaner roofline, and a more aggressive front end that gave the car real visual authority. When you add the Super Sport package and the 396 cubic-inch Turbo-Jet big block to that body, you have the combination that defined what a mid-size muscle car was supposed to be. This particular car is a convertible, which places it in a significantly smaller production subset than the hardtop. The 1966 Chevelle SS 396 convertible was not built in large numbers — Chevrolet produced considerably more hardtops than open-top SS 396 cars in 1966, making a restored example in this condition genuinely scarce. The Body by Fisher tag reads 13867, which is the GM body style code for the 1966 Chevelle Malibu SS convertible. That tag confirms this car's identity as a true factory convertible, not a hardtop conversion. The restoration on this car has already done its job at the show level. It has been judged and recognized as a show winner, which means it has been evaluated by people who know exactly what to look for. This is not a car that was cleaned up and photographed well — it has been through the process and came out on the right side of it. The combination of Rally Red exterior, Regal Red vinyl interior, white convertible top, and the 396 big block under the hood is the kind of specification that collectors actively search for. The 396 cubic-inch big block V8 has been one of the most respected engines in American performance history since Chevrolet introduced it in 1965. In 1966, the 396 was offered in the Chevelle SS in multiple states of tune, ranging from 325 horsepower up to 360 horsepower in the top L78 configuration. The Turbo-Jet 396 badges on this car's fenders reflect the factory designation Chevrolet used for this engine family throughout the mid-to-late 1960s. The block installed in this car is a 1969 GM unit, which is a well-regarded choice among builders working with the Mark IV big block family. The 396 architecture shares its basic block design with the larger 427 and 454 that came later, and all of them benefit from the same robust bottom-end engineering that made these engines reliable under hard use. The engine compartment presents cleanly, with chrome valve covers complementing the correct orange engine finish and the period-correct Turbo-Jet air cleaner assembly visible in every engine photo. Cooling is handled by an Alloyworks aluminum radiator combined with an electric fan, a practical upgrade that provides meaningfully better heat rejection than the original copper-brass unit while eliminating the parasitic drag of a mechanical fan. This is a sensible choice on a car that will see warm-weather driving in Florida. Backing the 396 is a Turbo-Hydramatic TH400 automatic transmission — one of the strongest automatics GM ever produced. The TH400 was a three-speed unit used across GM's performance and heavy-duty lineup from 1964 onward and was the preferred transmission for big block applications. Out back, a GM 12-bolt rear end handles the load. The 12-bolt was the stronger of GM's two rear axle designs of the era and was specifically paired with higher-output engines and performance packages. The underside of this car is coated and clean, and the undercarriage photos confirm a straight, well-finished floor and frame with no visible rust or deferred repair work. Stopping is handled by power front disc brakes, a critical upgrade given the weight and output of the 396. Disc brakes were not standard equipment on the 1966 Chevelle SS — they were an option that many buyers skipped — and having them on this car is a meaningful functional advantage. Rear suspension has been upgraded with new shocks, and the dual exhaust system exits cleanly at the rear. The car rolls on US Mags chrome wheels measuring 20 inches at the front and 18 inches at the rear, fitted with Lexani performance tires. The 1966 Chevelle SS 396 convertible interior is finished in Regal Red vinyl throughout — seats, door panels, carpet, and rear seat. The color match between the interior and the Rally Red exterior is tight and deliberate, and the result in person is as visually coherent as it looks in the photos. The vinyl shows no visible cracking, fading, or misalignment in the panel fits. The seams on both the front bucket seats and the rear bench are straight and even, which is one of the details that separates a quality restoration from a cosmetic one. The dashboard carries the SS gauge package, which was a factory option on the 1966 Chevelle Super Sport. This cluster replaced the standard base gauges with instrumentation that gave the driver actual readings for fuel level and other functions rather than relying on warning lights. The column-mounted tachometer is visible in the interior photos — a round, chrome-ringed gauge mounted at the top of the steering column, reading in hundreds of RPM. This was a factory-available option on the 1966 SS and is exactly correct for this application. The sport steering wheel fits the period correctly, and the Super Sport dash badge is intact and clearly legible. Air conditioning controls are integrated into the dashboard, and a custom audio system has been added in a location that does not compromise the overall appearance of the interior. The power convertible top mechanism is operational, and the white soft top is in clean condition. With the top down, the all-red interior is fully visible, which is clearly the intended presentation for this car. The 1966 Chevelle SS 396 wears Rally Red paint applied using a PPG base/clear system. Base/clear application provides better depth and durability than single-stage paint and responds well to polishing and maintenance over time. The finish in the photos shows consistent color across all panels with no visible orange peel, runs, or color variation at the seams. The Super Sport exterior identification on this car is complete. The blacked-out grille carries the SS 396 badge in the center, which is correct for the 1966 model year. Turbo-Jet 396 fender emblems are present on both front quarters. The rear bumper area shows the Chevelle SS 396 badging on the trunk lid panel between the taillights, which is a detail that matters when a car is being evaluated for authenticity. Bumper guards are fitted at both ends, which was a period accessory and protects the chrome during normal use. The SS hood vent design is one of the most recognizable styling elements on the 1966 Chevelle — a pair of non-functional vents stamped into the hood that give the car a more aggressive profile than the base Chevelle. They are cleanly finished here and properly aligned with the body lines on either side. The white convertible top, when raised, contrasts directly with the Rally Red body and provides a color break that works well with this particular specification. Chrome is present on the bumpers, window surrounds, door handles, and mirror housing. All of it appears clean and reflective in the photos, with no visible pitting or rust. The underside photos confirm a coated and protected floor pan with no patching or irregularity visible. The 1966 Chevrolet Chevelle SS 396 convertible represents a specific intersection of body style, engine, and model year that has a dedicated following among serious collectors. Convertibles are inherently less common than hardtops in any muscle car population, and they deteriorate faster — which means a fully restored example with a correct big block, a verified factory body tag, and a show-level finish is not something that comes up regularly at this standard. This car has been through the restoration process completely, has been judged against other cars in a show environment, and presents consistently in every area from the engine compartment to the undercarriage to the interior. If you are looking at a 1966 Chevelle SS 396 convertible, the details on this car hold up under scrutiny. To schedule a walk-around or ask specific questions, call Skyway Classics in Sarasota, Florida at 941-254-6608. Our team is here to help.

Mileage: 9,011 mi
Transmission: 3-Speed Automatic
Body Type: Convertible
VIN: 138676B167267
Stock #: MIU28685
Location: Sarasota, FL