1992 Benetton B192

The Grand Prix de Monaco Historique is a celebration of not only historic motorsport but also one of the most loved circuits in the world. And it’s only right to start off the list with a Formula 1 car. The first is this Benetton B192 (est. 550,000–750,000 euros), which was raced by Michael Schumacher in Spain, where he qualified an impressive 2nd. And while this would be its only Formula 1 outing, it’s the first Formula 1 chassis on which Schumacher, Rory Byrne, and Ross Brawn worked together — a collaboration that would go on to win seven Drivers’ and six Constructors’ World Championship titles.

1991 Ruf RCT Evo

Since the emergence of the ‘Yellowbird’ in 1987, Ruf has been the go-to tuner for Porsche. This yellow 1991 Porsche 964 Turbo (180,000–220,000 euro) was sent to the Ruf factory in 2015 for a full RCT Evo conversion, which included an upgraded 3.6-litre flat six engine and six-speed manual transmission, Ruf instruments, fully adjustable suspension, five-spoke Ruf wheels, and a rear spoiler. The car’s interior features a leather and Alcantara interior and shows just 3,000km on its odometer since its conversion.

1957 Ferrari 250 GT Berlinetta Compitizione ‘Tour de France’

Delivered new to Ferrari factory driver Wolfgang Seidel, this Ferrari 250 GT Berlinetta Compitizione ‘Tour de France’ (7–9m euros) was the 15th of 17 third-series examples with desirable covered headlights. As you'd expect, the car competed in numerous events around the world, including the 1958 Grand Prix of Spa-Francorchamps, where it finished 2nd overall, and the 1958 12 Hours of Reims, where it finished 4th overall. With only two caretakers in the last 45 years, the car is fully matching numbers and Ferrari Classiche certified — a truly beautiful example.

1973 Porsche 911 Carrera RS 2.7 Lightweight

This 1973 Porsche 911 Carrera RS 2.7 Lightweight (1.4–1.8m euros) was built by the factory for Finnish racing and rally driver Leo Kinnunen and, at his request, was fitted with larger ‘ST’-style wheel arches to accommodate wider wheels and tyres — one of only two to be built with this feature; although, this is the only 2.7 RS with a ‘tea-tray’ 1974 Carrera 3.0 RS rear fin. Kinnunen also specified a larger-than-normal steering wheel and a raised passenger seat. Along with these unique options, this RS was also fitted such racing options as a limited-slip differential, an alloy roll cage, Recaro rally seats, and Repa racing harnesses.

2018 Lamborghini Huracán

While a new Lamborghini Huracán wouldn’t typically make our top five list, this particular example (250,000 – 350,000 euros) is extra special, as it was delivered directly to the Holy Father, Pope Francis. Built and customised by Lamborghini's Ad Personam program, the Huracán is finished in Bianco Monocerus with Giallo Tiberino stripes and interior wrapped in Bianco Leda Sportivo leather, with Lamborghini crests adorning the headrests. The car features details in the colours of the Vatican City flag, 20-inch Giano wheels, and Nero brake callipers. The bonnet has been signed by the Pope himself and all proceeds will benefit a number of charities selected by His Holiness.

Photos: RM Sotheby’s