After the first 40 cars had been produced, a second series was created. To differentiate it from the more sporting 250 GT Spider California, the Cabriolet’s styling was made more sober, boot space was increased and it was made more comfortable inside. Production continued until 1962, and around 200 cars were built in all. Although there had been many successful spider-bodied Ferraris by the late fifties, cabriolets featuring proper folding soft tops had only been produced in relatively small numbers. Most of these were at the beginning of the decade, apart from subsequent, occasional one-off examples at the request of a specific client or as a design study on a show car. When Carrozzeria Boano exhibited a 250 GT Cabriolet, chassis 0461GT, at the 1956 Geneva Salon, it was the beginning of a new era for this style of car in the Ferrari production programme, which led to the first series of Pininfarina-designed cabriolets produced during 1957 and 1958.

The body was mounted on the same 2600 mm wheel base chassis as the concurrently produced 250 GT ‘Boano’ and ’Ellena’ coupés, with factory type reference number 508C. All had chassis numbers in the odd number road car sequence carrying a ’GT’ suffix, constructed along similar lines to the coupés, with the same mechanical components, like suspension, brakes, and steering.

One of the early prototype examples produced by Pininfarina was more a spider than a cabriolet, as there was no provision for a folding hood on chassis 0663GT, which had a removable metal tonneau panel over the passenger area, with a low Plexiglass windscreen devoid of wipers, and a driver’s headrest that flowed into the tail panel, as on the sports racing cars of the period. The Pininfarina design was very elegant and beautifully balanced, similar in appearance to the two coupé ‘Speciale’ examples produced on chassis numbers 0725GT and 0751GT, whose design was undoubtedly influenced by these cabriolets. The model generally featured covered headlights in the wing extremities, although some later examples had open headlights due to a change in Italian lighting legislation, with vertical rubber-faced bumperettes below them, flanking the wide and low shallow oval egg-crate grille. The front wing line flowed through the door, with a curve up to the lightly finned rear wing line, which terminated with a triangular, flush mounting tail light in the top trailing edge. 

The Pininfarina move towards uniformity continued with these cabriolets, although as with the coupés produced around the same time, individual cars were personalised for particular clients. At the 1958 Paris Salon the model was exhibited in a mildly modified form, in that the vertical front bumperettes had been replaced by a full-width chrome-plated bumper that ran below the grille. The bodies were constructed and trimmed by Pininfarina, before shipment to Ferrari for fitment of the mechanical components. A total of forty examples were built including the prototypes, in the chassis range of 0655GT to 1475GT, all but two of which were left-hand drive. 
The single overhead camshaft per bank 3-litre V12 engine, with factory type reference 128C, was identical to that used in the concurrent coupés, as was the gearbox and drive-train. The first prototype, chassis 0655GT, which featured a cut-out in the top of the driver’s door to provide an arm rest, became the property of a Ferrari works racing driver, the Englishman Peter Collins.
When he brought the car to England, he commissioned the installation of Dunlop disc brakes, and legend has it that upon returning to Italy, Ferrari dismantled the disc brake set-up from his car and borrowed it to use on a 250 Testa Rossa sports racing car for test purposes. The engineers must have been impressed, as by the end of 1959, four wheel disc brakes were standard on Ferrari road cars, having found their way onto the 250 Testa Rossa competition models at the beginning of the year.