The 39th reenactment of the 1000 Miglia is only a few days away and this year Alfa Romeo will be sending a quartet of classics from its Heritage collection to the three-day tour of Italy. At the wheel of one will be John Elkann, the chairman of Stellantis which owns Alfa Romeo.

The chairman will be joined by his wife Lavinia Borromeo (whose family traces its noble line to the 1400s) in a 1956 Alfa Romeo 1900 Super Sprint, which is powered by a 4-cylinder engine with the brand’s characteristic twin-camshafts to help it produce 115 hp at 5,500 hp.

They will be accompanied by a 1928 Alfa Romeo 6C 1500 Super Sport, a 1954 Alfa Romeo 2000 Sportiva, and a 1956 Alfa Romeo 1900 Sport Spider.

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Although just two years younger than Elkann’s 1900, the 1954 1900 Sport Spider is noteworthy because it’s just one of two racing spiders ever produced. Its dry-sump twin-cam 1900 engine is supercharged, which helps it produce 138 hp. Along with the 880 kg curbweight, that power helps it get all the way up to a top speed of 220 km/h (136 mph). Featuring bodywork by Franco Scaglione of the Bertone workshop, a De Dion rear axle, and a 5-speed transmission, it was well ahead of its time in terms of performance and technology.

Similarly, there are only two 1954 Alfa Romeo 2000 Sportivas in existence. It features the same engine as the Sport Spider, along with much of the same technology, and it too sports bodywork by Franco Scaglione. Its curves, though, would come to inspire cars like the Giulietta Sprint.

Finally, the 6C 1500 Super Sport is of particular interest, since a similar model won the 1928 running of the 1000 Miglia with Giuseppe Campari and Giulio Ramponi. This model in particular, with bodywork by the Farina workshops, is also a winner, having most recently taken the top spot at the 2005, 2007, 2008, and 2019 editions of the race.

It’s powered by a 1487cc 6-cylinder engine that makes 76 hp at 4,800 rpm and can reach a top speed of 140 km/h (87 mph). One of 31 built between 1928 and 1929, it raced under the number 37 in its day.

Inspired by the long-distance road race that ran from 1927 to 1957, a regularity race for classic and vintage cars has taken place in the same area since 1977. The 2021 1000 Miglia starts on Wednesday, June 16, and runs until Saturday, June 19.